[ CAS No. 145881-74-9 ] {[proInfo.proName]}

Name: 145881-74-9|[2-(2-Hydroxy-ethoxy)-ethyl]-carbamic acid benzyl ester|95%
Brand: Ambeed
SKU: A235930
Price: 5.0 USD
Availability: InStock
Rating: 94 (30 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 145881-74-9 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 145881-74-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 145881-74-9 ]

SDS Specification

Alternatived Products of [ 145881-74-9 ]

Product Details of [ 145881-74-9 ]

CAS No. :	145881-74-9	MDL No. :	MFCD15143230
Formula :	C₁₂H₁₇NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NFPGZLVPTVWFSY-UHFFFAOYSA-N
M.W :	239.27	Pubchem ID :	11064482
Synonyms :

Calculated chemistry of [ 145881-74-9 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	9
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	62.17
TPSA :	67.79 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.66
Log Po/w (XLOGP3) :	0.61
Log Po/w (WLOGP) :	0.77
Log Po/w (MLOGP) :	0.7
Log Po/w (SILICOS-IT) :	1.33
Consensus Log Po/w :	1.21

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.37
Solubility :	10.1 mg/ml ; 0.0422 mol/l
Class :	Very soluble
Log S (Ali) :	-1.61
Solubility :	5.9 mg/ml ; 0.0247 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.33
Solubility :	0.111 mg/ml ; 0.000463 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.54

Safety of [ 145881-74-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 145881-74-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 145881-74-9 ]
Downstream synthetic route of [ 145881-74-9 ]

[ 145881-74-9 ] Synthesis Path-Upstream 1~3

1
[ 501-53-1 ]
[ 929-06-6 ]
[ 145881-74-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 10 - 20℃;	To a 3 -necked, 3 L flask equipped with an overhead stirrer, addition funnel, N₂ inlet, and temperature probe was added 3 (250 ml, 2340 mmol) and 2-Methyl-THF (1010 ml), and the mixture was cooled within ice- bath. A solution of benzyl chloroformate (167 ml, 1125 mmol) 1/2~2-Methyl-THF (323 ml) was added slowly over 40 min, maintaining the temperature below t0°C. After aging 1 hr at RT, the resulting milky mixture was added hydrochloric acid (1 M in EtOAc, 90 ml, 90 mmol) and aged for 30 min. White solid was removed by filtration through a pad of Solka Floc/Celite, and the filtrate was concentrated under vacuum to afford 4 as a light yellow oil (228 g, quantitative).
96%	With triethylamine In tetrahydrofuran at 20℃; for 1 h; Inert atmosphere	Example 27. Benzyl 2-(2-hydroxyethoxy)ethylcarbamate (29).; [0179] To a solution containing 1.01 g (9.61 mmol) of 2-(2-aminoethoxy)ethanol in 100 niL of THF at room temperature was added 1.34 mL of Et₃N and 1.49 mL of CbzCl. The reaction mixture was stirred for 1 h and diluted with 250 mL of ethyl acetate. The organic layer was washed with two 250-mL portions of H₂O, two 250-mL portions of brine, dried (MgSO₄), and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (30 cm x 4 cm). Elution with 9:1 ethyl acetate- hexanes afforded 29 as a colorless oil: yield 2.21 g (96percent); silica gel TLC i?/ 0.30 (9:1 ethyl acetate-hexanes); ¹H NMR (CDCl₃) δ 3.30 (m, 2H), 3.45 (m, 4H), 3.52 (s, IH), 3.62 (m, 2H), 5.03 (s, 2H), 5.86 (m, IH), and 7.27 (m, 5H); ¹³C NMR (CDCl₃) δ 40.54, 61.11, 66.31, 69.70, 71.96, 127.72, 127.75, 128.13, 136.28, and 156.50.
96%	With triethylamine In tetrahydrofuran at 20℃; for 1 h;	[02541 Benzyl 2 ~(2~Hy drox v eth ox v )et h vlca rbam ate (54). To a solution containing 1.01 g (9.61 mmol) of 2-(2-aniinoethoxy)ethanol in 1 0 mL of THF at room temperature was added 1.34 mL (9.61 mmol) of EtjN and 1.49 mL (1.78 g, 10.6 nunol) of CB Ci. The reaction mixture was stirred for 1 h and was then diluted with 250 mL of ethyl acetate. The organic layer was washed with two 250- mL portions of0, two 250-mL portions of brine, and was then dried (MgSi} and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (30 *· 4 cm). Elution with 9:1 ethyl acetate hexaues afforded alcohol 54 as a colorless oil: yield 2.21 g (96percent); silica gel TLC / 0.30 (9: 1 ethyl acetate--hexaaes); ^SH NMR (CDCK) 3.30 (m, 2H), 3.45 On, 4H), 3.52 (s, 1H), 3.62 (m, 2H), 5.03 (s, 2H), 5.86 (m, 1H) and 7.27 (m, 5H); ^t3C NMR (CDCfe) 40.5, 61 .1 , 66.3, 69.7, 72.0, 127.72; 127.75, 128.1 , 1 36.3 and 156.5.

96%	With triethylamine In tetrahydrofuran for 1 h;	To a solution containing 1.01 g (9.61 mmol) of 2-(2-aminoethoxy)ethanol in 100 mL of THF at room temperature was added 1.34 mL (9.61 mmol) of Et3N and 1.49 mL (1.78 g, 10.6 mmol) of CBzC1. The reaction mixture was stirred for 1 h and was then diluted with 250 mL of ethyl acetate. The organic layer was washed with two 250- mL portions of H20, two 250-mL portions of brine, and was then dried (MgSO4) and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (30 x 4 cm). Elution with 9:1 ethyl acetate—hexanes afforded alcohol 39 as a colorless oil: yield 2.21 g (96percent); silica gel TLC R0.30 (9:1 ethyl acetate—hexanes); ‘HNMR (CDC13) 3.30 (m, 2H), 3.45 (m, 4H), 3.52 (s, 1H), 3.62 (m, 2H), 5.03 (s, 2H), 5.86 (m, 1H) and 7.27 (m, 5H); ‘3C NMR (CDC13) 40.5, 61.1, 66.3, 69.7, 72.0, 127.72, 127.75, 128.1, 136.3 and156.5.
92%	With triethylamine In dichloromethane at 20℃; for 16 h; Cooling with ice	To the solution of 2-(2-aminoethoxy)ethanol (301 .0 g, 2.863mol, 1 .Oeq) in 1500ml_ DCM was added Et₃N (343. Og, 3.390mol, 1 .2eq) under the ice-water bath (control the temperature below 20°C), then CBz-CI (488. Og, 2.863mol, 1 .Oeq) was added dropwise to the above cooled solution (control inside temperature below 20°C). The resultant solution was stirred for overnight (>16 hrs) and then washed with water 1500 mL, sat. NaHC0₃ (1500 mL), 1 N HCI (1500 mL) and brine (1500 mL), respectively. The organic layer was dried (200 g of Na2S04) and concentrated for next step directly. Yield of product 639 g, 92percent. Colorless oil.
90%	With triethylamine In methanol at 0 - 20℃;	CBZ-Protected Amino Ethoxy Ethanol (S1) [0092] 1-amino-2-ethoxyethanol (1.358 mL, 9.5 mmol) was dissolved in 20 mL 10percent triethylamine in MeOH and cooled to 0° C. Benzyl chloroformate (0.946 mL, 9.5 mmol) was added all at once, and the reaction was allowed to warm to room temperature overnight. The solvent was removed by evaporation, and the product purified using silica column chromatography, resulting in a colorless oil (95percent yield). [0093] 1H NMR (500 MHz, CDCl3) 2.69 (bs, 1H), 3.36 (t, 2H), 3.50 (m, 4H), 3.67 (t, 2H), 5.07 (s, 2H), 5.78 (bs, 1H), 7.32 (m, 5H) [0094] 13C NMR (125 MHz, CDCl3) 40.83, 61.48, 66.71, 70.07, 72.27, 128.13, 128.51, 136.52, 156.81
87%	With triethylamine In dichloromethane at 5 - 20℃; Inert atmosphere	To a 500-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was added 2-(2-arninoethoxy)ethan-l -ol (16.1 g, 153 mmol, 1 equiv), CH2CI2 (160 mL), and triethylarnine (22.4 mL, 1.05 equiv). This was followed by the addition of CbzCI (28.7 g, 168.24 mmol, 1.1 equiv) dropwise with stirring at 5-10°C. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 100 mL of water and extracted with 3 x 100 mL of CH2CI2. The organic layers were combined and washed with 1 x 100 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The solid was dried in an oven under reduced pressure. The residue was applied onto a silica gel column with petroleum ether/ethyl acetate (1:1) providing 32 g (87percent) of benzyl N-[2-(2- bydroxyethoxy)ethyl] carbamate (INT-PI) as a yellow oil.
85%	With triethylamine In methanol at 20℃; for 20 h;	General procedure: The desired aminoalcohol (17 mmol, 2-(2-aminoethoxy)ethanol or 2-[2-(2-aminoethoxy)ethoxy]ethanol) was dissolved in CH₃OH (10 mL) and TEA (5.45 mL, 39.2 mmol) was added. To this solution, stirred at room temperature, was added dropwise a solution of benzyloxycarbonyl chloride (ZCl, 3.2 g, 18.77 mmol) in CH₃OH (5 mL). After the addition was complete the reaction mixture was stirred at room temperature for 20 h, protected from moisture with a CaCl₂ drying tube. The solvent was then evaporated and the crude was dissolved in CH₂Cl₂ (150 mL) and washed first with a 5percent aqueous solution of KHSO₄ (2 × 50 mL) and then with water (2 × 50 mL). The evaporation of the dried solvent (Na₂SO₄) afforded the product as a clear oil pure enough to be used in the following steps. 4.1.1 2-(N-Benzyloxycarbonyl-2-aminoethoxy)ethanol³¹ Yield 85percent; R_f = 0.35 (CH₂Cl₂/CH₃OH 9.5:0.5); ¹H NMR (CDCl₃) δ: 2.58 (br, 1H); 3.39 (q, 2H, J = 5.6 Hz); 3.52–3.59 (m, 4H); 3.69–3.76 (m, 2H); 5.09 (s, 2H); 5.42 (br, 1H); 7.31–7.35 (m, 5H); ¹³C NMR (CDCl₃) δ: 40.8 (t); 61.6 (t); 66.7 (t); 70.1 (d); 72.2 (d); 128.1 (d); 128.5 (d); 136.4 (s); 156.6 (s); ESI-MS (m/z): 240.0 [M + H⁺]; 262.0 [M + Na⁺]; 278.0 [M + K⁺]; 257.0 [M + NH₄⁺].
45%	With sodium hydroxide In tetrahydrofuran; water at 4℃; for 2 h;	A solution of benzyl chloroformate (5.4 mL, 38.0 mmol) in THF (8.0 mL) was addeddropwise over 15 minutes to a solution of 2-(2-aminoethoxy)ethanol 10 (2.96 mL,29.6 mmol) in 0.8 M aqueous sodiumhydroxide (75 mL) at 4 C. The reaction wasstirred for 2 hours then quenched upon dropwise addition of 1.0 M aqueous HCl (25 mL). The ice-bath was removed and the mixture was extracted with ethyl acetate (3 x100 mL) and the combined organics were dried (MgSO4), filtered and concentrated invacuo. Purification by flash chromatography (50percent ethyl acetate in dichloromethane)provided the protected amine 11 (3.13 g, 45percent) as an orange oil. Rf 0.48 (100percent ethyl acetate); H (500 MHz; CDCl3) 7.37-7.29 (5H, m), 5.20 (1H, brs), 5.11 (2H, s), 3.74-3.69 (2H, m), 3.58-3.55 (4H, m), 3.41-3.38 (2H, m), 1.99 (1H, brs). This data corresponds well with previously reported data.305 The compound was notcharacterised further.
52 g	With triethylamine In methanol at 0 - 20℃; for 12 h;	2-(2-aminoethoxy)ethanol (25.23 g, 0.240 mol) was dissolved in 530 mL of 10percent triethylamine in MeOH (48 ml, 0.345 mol of triethylamine, 480 ml of methanol) and cooled to 0 °C. Benzyl chloroformate (technical grade, 95percent, 34.4 ml, 0.229 mol) was added all at once, and the reaction was allowed to warm to room temperature. After 12 h, the solvent was removed by evaporation, and the product purified using silica column chromatography (ethyl acetate/hexane), resulting in a colorless oil (6*, 52 g, 0.163 mol, 95percent based on benzyl chloroformate). The crude material was analytically pure as analyzed by LC/MS and TLC, and was used in the next step with no further purification. MS m/z 239.17 (M+1)⁺ (239.12 calculated).

Reference： [1] Patent: WO2011/53614, 2011, A1, . Location in patent: Page/Page column 9
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 41, p. 10310 - 10323
[3] Patent: WO2011/19419, 2011, A1, . Location in patent: Page/Page column 60
[4] Journal of the American Chemical Society, 2013, vol. 135, # 8, p. 2883 - 2886
[5] Patent: WO2014/145109, 2014, A1, . Location in patent: Paragraph 0254
[6] Patent: WO2014/152718, 2014, A1, . Location in patent: Paragraph 0237; 0247
[7] Journal of the American Chemical Society, 2011, vol. 133, # 41, p. 16346 - 16349
[8] Patent: WO2018/6063, 2018, A1, . Location in patent: Page/Page column 177
[9] Patent: US2013/302258, 2013, A1, . Location in patent: Paragraph 0091; 0092; 0093; 0094
[10] Patent: WO2018/129552, 2018, A1, . Location in patent: Paragraph 0424
[11] Tetrahedron, 2017, vol. 73, # 21, p. 3014 - 3024
[12] Tetrahedron, 1996, vol. 52, # 15, p. 5591 - 5606
[13] Synlett, 2016, vol. 27, # 1, p. 121 - 125
[14] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 19, p. 5194 - 5198
[15] Patent: EP1184373, 2002, A1, . Location in patent: Example 92
[16] Patent: EP2957563, 2015, A1, . Location in patent: Paragraph 0082; 0083

2
[ 501-53-1 ]
[ 929-06-6 ]
[ 145881-74-9 ]

Yield	Reaction Conditions	Operation in experiment
67.5%	With sodium hydroxide In water	EXAMPLE 15 N-{2-12-(4-Chloro-phenoxy)-ethoxy]-ethyl}-N'-cyano-N"-pyridin-4-yl-guanidine (SBR-11-4433) was synthesised as follows 2-(2-Aminoethoxy)ethanol (5.26 g, 50 mmol) and sodium hydroxide (2.1 g, 52.5 mmol) were dissolved in water (200 mL). The resulted solution was cooled in ice bath, followed by the dropwise addition of benzyl chloroformate. After the addition, the reaction mixture was continuously stirred in ice bath for another hour. The desired product was extracted with ethyl acetate (EtOAc, 200 mL). The EtOAc layer was washed with water (3*100 mL) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo to yield the crude product. The product was further purified by flash column chromatography (SiO₂, 1:2 Hexane:EtOAc) to give [2-(2-hydroxy-ethoxy)-ethyl]-carbamic acid benzyl ester as a clear oil (8.07 g, 67.5percent yield). ¹H-NMR (CDCl₃, ppm) 7.35 (m, 5H), 5.34 (b, 1H), 5.10 (s, 2H), 3.71 (m, 2H), 3.56 (m, 4H), 3.41 (m, 2H), 2.20 (b 1H),. ESMS 240.0 (M+1).

Reference： [1] Patent: US6255323, 2001, B1,

3
[ 13139-17-8 ]
[ 929-06-6 ]
[ 145881-74-9 ]

Yield	Reaction Conditions	Operation in experiment
40 g	With triethylamine In dichloromethane at 20℃;	To 2-(2-aminoethoxyl)ethanol (20 g) dissolved in dichloromethane (200 ml) was added stepwise triethylamine (26.5 ml) and benzyloxy(carbonyloxy)succinimide (47.47 g). The reaction mixture was stirred overnight at room temperature. The solvent was distilled off under reduced pressure and the residue was dissolved in deionized water (500 ml). The insoluble layer was separated, and the aqueous layer was mixed with 50 g of NaCl and the pH adjusted to 5.0 with 5percent H₃PO₄. The product was extracted with dichloromethane (100 ml, 50 ml, and 50 ml) and the extract was dried with MgSO₄, filtered, and evaporated to dryness under reduced pressure. The residue was dried under vacuum overnight, then combined with the previously separated insoluble layer and dissolved in dichloromethane (300 ml). The solution was washed with 5-percent aqueous NaCl solution (3×50 ml) and dried with MgSO₄. The solvent was distilled under reduced pressure, and the residue was dried overnight under vacuum, giving 40 g of the desired product.

Reference： [1] Patent: US9173951, 2015, B2, . Location in patent: Page/Page column 125

[ 145881-74-9 ] Synthesis Path-Downstream 1~74

1
[ 4058-26-8 ]
[ 145881-74-9 ]
[ 149636-40-8 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 5591 - 5606

2
[ 501-53-1 ]
[ 929-06-6 ]
[ 145881-74-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	In 2-methyl-THF; at 10 - 20℃;	To a 3 -necked, 3 L flask equipped with an overhead stirrer, addition funnel, N2 inlet, and temperature probe was added 3 (250 ml, 2340 mmol) and 2-Methyl-THF (1010 ml), and the mixture was cooled within ice- bath. A solution of benzyl chloroformate (167 ml, 1125 mmol) ½~2-Methyl-THF (323 ml) was added slowly over 40 min, maintaining the temperature below t0C. After aging 1 hr at RT, the resulting milky mixture was added hydrochloric acid (1 M in EtOAc, 90 ml, 90 mmol) and aged for 30 min. White solid was removed by filtration through a pad of Solka Floc/Celite, and the filtrate was concentrated under vacuum to afford 4 as a light yellow oil (228 g, quantitative).
96%	With triethylamine; In tetrahydrofuran; at 20℃; for 1h;Inert atmosphere;	Example 27. Benzyl 2-(2-hydroxyethoxy)ethylcarbamate (29).; [0179] To a solution containing 1.01 g (9.61 mmol) of 2-(2-aminoethoxy)ethanol in 100 niL of THF at room temperature was added 1.34 mL of Et3N and 1.49 mL of CbzCl. The reaction mixture was stirred for 1 h and diluted with 250 mL of ethyl acetate. The organic layer was washed with two 250-mL portions of H2O, two 250-mL portions of brine, dried (MgSO4), and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (30 cm x 4 cm). Elution with 9:1 ethyl acetate- hexanes afforded 29 as a colorless oil: yield 2.21 g (96%); silica gel TLC i?/ 0.30 (9:1 ethyl acetate-hexanes); 1H NMR (CDCl3) delta 3.30 (m, 2H), 3.45 (m, 4H), 3.52 (s, IH), 3.62 (m, 2H), 5.03 (s, 2H), 5.86 (m, IH), and 7.27 (m, 5H); 13C NMR (CDCl3) delta 40.54, 61.11, 66.31, 69.70, 71.96, 127.72, 127.75, 128.13, 136.28, and 156.50.
96%	With triethylamine; In tetrahydrofuran; at 20℃; for 1h;	[02541 Benzyl 2 ~(2~Hy drox v eth ox v )et h vlca rbam ate (54). To a solution containing 1.01 g (9.61 mmol) of 2-(2-aniinoethoxy)ethanol in 1 0 mL of THF at room temperature was added 1.34 mL (9.61 mmol) of EtjN and 1.49 mL (1.78 g, 10.6 nunol) of CB Ci. The reaction mixture was stirred for 1 h and was then diluted with 250 mL of ethyl acetate. The organic layer was washed with two 250- mL portions of0, two 250-mL portions of brine, and was then dried (MgSi} and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (30 *· 4 cm). Elution with 9:1 ethyl acetate hexaues afforded alcohol 54 as a colorless oil: yield 2.21 g (96%); silica gel TLC / 0.30 (9: 1 ethyl acetate--hexaaes); SH NMR (CDCK) 3.30 (m, 2H), 3.45 On, 4H), 3.52 (s, 1H), 3.62 (m, 2H), 5.03 (s, 2H), 5.86 (m, 1H) and 7.27 (m, 5H); t3C NMR (CDCfe) 40.5, 61 .1 , 66.3, 69.7, 72.0, 127.72; 127.75, 128.1 , 1 36.3 and 156.5.

96%	With triethylamine; In tetrahydrofuran; for 1h;	To a solution containing 1.01 g (9.61 mmol) of 2-(2-aminoethoxy)ethanol in 100 mL of THF at room temperature was added 1.34 mL (9.61 mmol) of Et3N and 1.49 mL (1.78 g, 10.6 mmol) of CBzC1. The reaction mixture was stirred for 1 h and was then diluted with 250 mL of ethyl acetate. The organic layer was washed with two 250- mL portions of H20, two 250-mL portions of brine, and was then dried (MgSO4) and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (30 x 4 cm). Elution with 9:1 ethyl acetate-hexanes afforded alcohol 39 as a colorless oil: yield 2.21 g (96%); silica gel TLC R0.30 (9:1 ethyl acetate-hexanes); ?HNMR (CDC13) 3.30 (m, 2H), 3.45 (m, 4H), 3.52 (s, 1H), 3.62 (m, 2H), 5.03 (s, 2H), 5.86 (m, 1H) and 7.27 (m, 5H); ?3C NMR (CDC13) 40.5, 61.1, 66.3, 69.7, 72.0, 127.72, 127.75, 128.1, 136.3 and156.5.
92%	With triethylamine; In dichloromethane; at 20℃; for 16h;Cooling with ice;	To the solution of 2-(2-aminoethoxy)ethanol (301 .0 g, 2.863mol, 1 .Oeq) in 1500ml_ DCM was added Et3N (343. Og, 3.390mol, 1 .2eq) under the ice-water bath (control the temperature below 20C), then CBz-CI (488. Og, 2.863mol, 1 .Oeq) was added dropwise to the above cooled solution (control inside temperature below 20C). The resultant solution was stirred for overnight (>16 hrs) and then washed with water 1500 mL, sat. NaHC03 (1500 mL), 1 N HCI (1500 mL) and brine (1500 mL), respectively. The organic layer was dried (200 g of Na2S04) and concentrated for next step directly. Yield of product 639 g, 92%. Colorless oil.
90%	With triethylamine; In methanol; at 0 - 20℃;	CBZ-Protected Amino Ethoxy Ethanol (S1) [0092] 1-amino-2-ethoxyethanol (1.358 mL, 9.5 mmol) was dissolved in 20 mL 10% triethylamine in MeOH and cooled to 0 C. Benzyl chloroformate (0.946 mL, 9.5 mmol) was added all at once, and the reaction was allowed to warm to room temperature overnight. The solvent was removed by evaporation, and the product purified using silica column chromatography, resulting in a colorless oil (95% yield). [0093] 1H NMR (500 MHz, CDCl3) 2.69 (bs, 1H), 3.36 (t, 2H), 3.50 (m, 4H), 3.67 (t, 2H), 5.07 (s, 2H), 5.78 (bs, 1H), 7.32 (m, 5H) [0094] 13C NMR (125 MHz, CDCl3) 40.83, 61.48, 66.71, 70.07, 72.27, 128.13, 128.51, 136.52, 156.81
87%	With triethylamine; In dichloromethane; at 5 - 20℃;Inert atmosphere;	To a 500-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was added 2-(2-arninoethoxy)ethan-l -ol (16.1 g, 153 mmol, 1 equiv), CH2CI2 (160 mL), and triethylarnine (22.4 mL, 1.05 equiv). This was followed by the addition of CbzCI (28.7 g, 168.24 mmol, 1.1 equiv) dropwise with stirring at 5-10C. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 100 mL of water and extracted with 3 x 100 mL of CH2CI2. The organic layers were combined and washed with 1 x 100 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The solid was dried in an oven under reduced pressure. The residue was applied onto a silica gel column with petroleum ether/ethyl acetate (1:1) providing 32 g (87%) of benzyl N-[2-(2- bydroxyethoxy)ethyl] carbamate (INT-PI) as a yellow oil.
87.9%	With sodium hydrogencarbonate; In water; acetonitrile; at 0 - 20℃; for 12h;	To a solution of 2-(2-aminoethoxy)ethanol (5.00 g, 47.5 mmol, 4.76 mL, CAS929-06-6) and NaHCO3 (11.9 g, 142 mmol, 5.55 mL) in MeCN (50 mL) and H2O (50 mL) was added CbzCl (9.74 g, 57.07 mmol, 8.11 mL) dropwise at 0 C. The reaction mixture was stirred at 20 C. for 12 hours. On completion, the mixture was filtered, the filtrate was extracted with EA (2×100 mL), and the organic phase was concentrated in vacuo to give a residue. The residue was purified by flash silica gel chromatography to give the title compound (10.0 g, 87.9% yield) as yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.38-7.29 (m, 5H), 5.55 (s, 1H), 5.10 (s, 2H), 3.73-3.69 (m, 2H), 3.57-3.51 (m, 4H), 3.40 (q, J=5.2 Hz, 2H), 2.84 (s, 1H).
85%	With triethylamine; In methanol; at 20℃; for 20h;	General procedure: The desired aminoalcohol (17 mmol, 2-(2-aminoethoxy)ethanol or 2-[2-(2-aminoethoxy)ethoxy]ethanol) was dissolved in CH3OH (10 mL) and TEA (5.45 mL, 39.2 mmol) was added. To this solution, stirred at room temperature, was added dropwise a solution of benzyloxycarbonyl chloride (ZCl, 3.2 g, 18.77 mmol) in CH3OH (5 mL). After the addition was complete the reaction mixture was stirred at room temperature for 20 h, protected from moisture with a CaCl2 drying tube. The solvent was then evaporated and the crude was dissolved in CH2Cl2 (150 mL) and washed first with a 5% aqueous solution of KHSO4 (2 × 50 mL) and then with water (2 × 50 mL). The evaporation of the dried solvent (Na2SO4) afforded the product as a clear oil pure enough to be used in the following steps. 4.1.1 2-(N-Benzyloxycarbonyl-2-aminoethoxy)ethanol31 Yield 85%; Rf = 0.35 (CH2Cl2/CH3OH 9.5:0.5); 1H NMR (CDCl3) delta: 2.58 (br, 1H); 3.39 (q, 2H, J = 5.6 Hz); 3.52-3.59 (m, 4H); 3.69-3.76 (m, 2H); 5.09 (s, 2H); 5.42 (br, 1H); 7.31-7.35 (m, 5H); 13C NMR (CDCl3) delta: 40.8 (t); 61.6 (t); 66.7 (t); 70.1 (d); 72.2 (d); 128.1 (d); 128.5 (d); 136.4 (s); 156.6 (s); ESI-MS (m/z): 240.0 [M + H+]; 262.0 [M + Na+]; 278.0 [M + K+]; 257.0 [M + NH4+].
45%	With sodium hydroxide; In tetrahydrofuran; water; at 4℃; for 2h;	A solution of benzyl chloroformate (5.4 mL, 38.0 mmol) in THF (8.0 mL) was addeddropwise over 15 minutes to a solution of 2-(2-aminoethoxy)ethanol 10 (2.96 mL,29.6 mmol) in 0.8 M aqueous sodiumhydroxide (75 mL) at 4 C. The reaction wasstirred for 2 hours then quenched upon dropwise addition of 1.0 M aqueous HCl (25 mL). The ice-bath was removed and the mixture was extracted with ethyl acetate (3 x100 mL) and the combined organics were dried (MgSO4), filtered and concentrated invacuo. Purification by flash chromatography (50% ethyl acetate in dichloromethane)provided the protected amine 11 (3.13 g, 45%) as an orange oil. Rf 0.48 (100% ethyl acetate); H (500 MHz; CDCl3) 7.37-7.29 (5H, m), 5.20 (1H, brs), 5.11 (2H, s), 3.74-3.69 (2H, m), 3.58-3.55 (4H, m), 3.41-3.38 (2H, m), 1.99 (1H, brs). This data corresponds well with previously reported data.305 The compound was notcharacterised further.
41.85%	With triethylamine; In tetrahydrofuran; at 20℃;Inert atmosphere; Cooling with ice;	1) Under nitrogen protection, 15 mL of diethylene glycol amine and 22.9 mL of triethylamine were dissolved in 150 mL of tetrahydrofuran. Under ice-bath conditions, 23.19 mL of benzyl chloroformate was slowly added dropwise, and stirred at room temperature overnight. The reaction was detected by TLC After completion, it was diluted with water and extracted with ethyl acetate, dried over anhydrous magnesium sulfate and concentrated. EA: PE = 8: 1 was passed through the column to obtain 15 g of compound 2. The yield was 41.85%.
52 g	With triethylamine; In methanol; at 0 - 20℃; for 12h;	2-(2-aminoethoxy)ethanol (25.23 g, 0.240 mol) was dissolved in 530 mL of 10% triethylamine in MeOH (48 ml, 0.345 mol of triethylamine, 480 ml of methanol) and cooled to 0 C. Benzyl chloroformate (technical grade, 95%, 34.4 ml, 0.229 mol) was added all at once, and the reaction was allowed to warm to room temperature. After 12 h, the solvent was removed by evaporation, and the product purified using silica column chromatography (ethyl acetate/hexane), resulting in a colorless oil (6*, 52 g, 0.163 mol, 95% based on benzyl chloroformate). The crude material was analytically pure as analyzed by LC/MS and TLC, and was used in the next step with no further purification. MS m/z 239.17 (M+1)+ (239.12 calculated).

Reference： [1]Patent: WO2011/53614,2011,A1 .Location in patent: Page/Page column 9
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 10310 - 10323
[3]Patent: WO2011/19419,2011,A1 .Location in patent: Page/Page column 60
[4]Journal of the American Chemical Society,2013,vol. 135,p. 2883 - 2886
[5]Patent: WO2014/145109,2014,A1 .Location in patent: Paragraph 0254
[6]Patent: WO2014/152718,2014,A1 .Location in patent: Paragraph 0237; 0247
[7]Journal of the American Chemical Society,2011,vol. 133,p. 16346 - 16349
[8]Patent: WO2018/6063,2018,A1 .Location in patent: Page/Page column 177
[9]Biomacromolecules,2020,vol. 21,p. 793 - 802
[10]Patent: US2013/302258,2013,A1 .Location in patent: Paragraph 0091; 0092; 0093; 0094
[11]MedChemComm,2019,vol. 10,p. 1037 - 1041
[12]Patent: WO2018/129552,2018,A1 .Location in patent: Paragraph 0424
[13]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 2956; 2957
[14]Tetrahedron,2017,vol. 73,p. 3014 - 3024
[15]Chemical Communications,2019,vol. 55,p. 1821 - 1824
[16]Tetrahedron,1996,vol. 52,p. 5591 - 5606
[17]Synlett,2016,vol. 27,p. 121 - 125
[18]Patent: CN110372765,2019,A .Location in patent: Paragraph 0047; 0048-0049
[19]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5194 - 5198
[20]Patent: EP1184373,2002,A1 .Location in patent: Example 92
[21]Patent: EP2957563,2015,A1 .Location in patent: Paragraph 0082; 0083

3
[ 5292-43-3 ]
[ 145881-74-9 ]
N-(benzyloxycarbonyl)-2-(2-(2-aminoethoxy)ethoxy)acetate tert-butyl ester [ No CAS ]
{benzyloxycarbonyl-[2-(2-tert-butoxycarbonylmethoxy-ethoxy)-ethyl]-amino}-acetic acid tert-butyl ester [ No CAS ]

Reference： [1]Organic Preparations and Procedures International,2002,vol. 34,p. 326 - 331

4
[ 5292-43-3 ]
[ 145881-74-9 ]
N-(benzyloxycarbonyl)-2-(2-(2-aminoethoxy)ethoxy)acetate tert-butyl ester [ No CAS ]
{benzyloxycarbonyl-[2-(2-tert-butoxycarbonylmethoxy-ethoxy)-ethyl]-amino}-acetic acid tert-butyl ester [ No CAS ]
[2-(2-benzyloxycarbonylamino-ethoxy)-ethoxy]-acetic acid 2-(2-benzyloxycarbonylamino-ethoxy)-ethyl ester [ No CAS ]
[benzyloxycarbonyl-(2-{2-[2-(2-benzyloxycarbonylamino-ethoxy)-ethoxycarbonylmethoxy]-ethoxy}-ethyl)-amino]-acetic acid tert-butyl ester [ No CAS ]

Reference： [1]Organic Preparations and Procedures International,2002,vol. 34,p. 326 - 331

5
[ 524-38-9 ]
[ 145881-74-9 ]
{2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-ethyl}-carbamic acid benzyl ester [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2005,vol. 16,p. 15 - 19

6
[ 145881-74-9 ]
[2-(2-aminooxy-ethoxy)-ethyl]-carbamic acid benzyl ester [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2005,vol. 16,p. 15 - 19
[2]Patent: US9173951,2015,B2

7
[ 145881-74-9 ]
t-butyl 2-(2-benzyloxycarbonylaminoethoxy)ethoxycarbamate [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2005,vol. 16,p. 15 - 19

8
[ 145881-74-9 ]
2-[2-(N-benzyloxycarbonyl)aminoethoxy]ethoxyacetic acid [ No CAS ]

Reference： [1]Organic Preparations and Procedures International,2002,vol. 34,p. 326 - 331
[2]Organic Preparations and Procedures International,2002,vol. 34,p. 326 - 331

9
[ 145881-74-9 ]
[ 149636-42-0 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 5591 - 5606

10
[ 145881-74-9 ]
[ 149665-63-4 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 5591 - 5606

11
[ 145881-74-9 ]
(2S,5R,6R)-6-{2-[2-(2-Benzyloxycarbonylamino-ethoxy)-ethoxy]-ethanesulfonylamino}-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 5591 - 5606

12
[ 145881-74-9 ]
[ 149636-43-1 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 5591 - 5606

13
[ 145881-74-9 ]
Sodium; 2-[2-(2-benzyloxycarbonylamino-ethoxy)-ethoxy]-ethanesulfonate [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 5591 - 5606

14
[ 501-53-1 ]
[ 929-06-6 ]
N-{2-12-(4-Chloro-phenoxy)-ethoxy]-ethyl}-N'-cyano-N"-pyridin-4-yl-guanidine [ No CAS ]
[ 145881-74-9 ]

Yield	Reaction Conditions	Operation in experiment
67.5%	With sodium hydroxide; In water;	EXAMPLE 15 N-{2-12-(4-Chloro-phenoxy)-ethoxy]-ethyl}-N'-cyano-N"-pyridin-4-yl-guanidine (SBR-11-4433) was synthesised as follows 2-(2-Aminoethoxy)ethanol (5.26 g, 50 mmol) and sodium hydroxide (2.1 g, 52.5 mmol) were dissolved in water (200 mL). The resulted solution was cooled in ice bath, followed by the dropwise addition of benzyl chloroformate. After the addition, the reaction mixture was continuously stirred in ice bath for another hour. The desired product was extracted with ethyl acetate (EtOAc, 200 mL). The EtOAc layer was washed with water (3*100 mL) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo to yield the crude product. The product was further purified by flash column chromatography (SiO2, 1:2 Hexane:EtOAc) to give [2-(2-hydroxy-ethoxy)-ethyl]-carbamic acid benzyl ester as a clear oil (8.07 g, 67.5% yield). 1H-NMR (CDCl3, ppm) 7.35 (m, 5H), 5.34 (b, 1H), 5.10 (s, 2H), 3.71 (m, 2H), 3.56 (m, 4H), 3.41 (m, 2H), 2.20 (b 1H),. ESMS 240.0 (M+1).

Reference： [1]Patent: US6255323,2001,B1

15
[ 106-48-9 ]
[ 145881-74-9 ]
[ 1972-28-7 ]
{2-[2-(4-chloro-phenoxy)-ethoxy]-ethyl}-carbamic acid benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99.8%	With triphenylphosphine; In tetrahydrofuran; hexane; ethyl acetate;	[2-(2-Hydroxy-ethoxy)-ethyl]-carbamic acid benzyl ester (2.39 g, 10 mmol), 4-chlorophenol (1.29 g, 10 mmol), and triphenylphosphine (2.89 g, 11 mmol) were dissolved in tetrahydrofuran (50 ml), followed by the dropwise addition of diethylazodicarboxylate (1.73 ml, 11 mmol). After the addition, the reaction solution was stirred at room temperature for 10-12 hours. The solvent was then removed in vacuo. The remaining residue was stirred in 30% EtOAc in hexane (200 mL) for 10 minutes and a white solid was formed. This solid was then filtered and washed with 30% EtOAc in hexane (3*20 mL). The filtrates were combined and the solvents were removed in vacuo. The remaining residue was purified by flash column chromatography (SiO2, 2:1 hexane:EtOAc) to give {2-[2-(4-chloro-phenoxy)-ethoxy]-ethyl}-carbamic acid benzyl ester as clear solid (3.49 g, 99.8% yield). 1H-NMR (CDCl3, ppm) 7.35 (m, 5H), 7.20 (d, 2H), 6.82 (d, 2H), 5.22 (b, 1H), 5.10 (s, 2H), 4.07 (t, 2H), 3.80 (t, 2H), 3.62 (t, 2H), 3.41 (q, 2H). ESMS 350.1 (M+l), 372.1 (M+23).

Reference： [1]Patent: US6255323,2001,B1

16
[ 302557-28-4 ]
[ 145881-74-9 ]
C₂₁H₃₁N₃O₃ [ No CAS ]

Reference： [1]Patent: EP1184373,2002,A1 .Location in patent: Example 92

17
[ 145881-74-9 ]
[ 1266609-56-6 ]

Reference： [1]Patent: WO2011/19419,2011,A1

18
[ 145881-74-9 ]
[ 1266609-57-7 ]

Reference： [1]Patent: WO2011/19419,2011,A1

19
[ 162111-91-3 ]
[ 145881-74-9 ]
[ 1266609-55-5 ]

Yield	Reaction Conditions	Operation in experiment
66%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;Inert atmosphere;	Example 28. (2iU^,4S,5S,6i0-2-(Acetoxymethyl)-4-(carbamoyloxy)-6-((2S,3S,4S,5^6S> 4,5-diacetoxy-6-(acetoxymethyl)-2-(2-(2-(benzyloxycarbonylamino)ethoxy)ethoxy) tetrahydro-2H-pyran-3-yloxy)tetrahydro-2H-pyran-3,5-diyl Diacetate (30).; [0180] To a solution containing 51 mg (59 mumol) of 27 in 7.5 niL Of CH2Cl2 was added a solution of 15 mg (65 mumol) of 29 in 7.5 ml of CH2Cl2 at 0 0C. To this cooled solution was added 0.07 mL (0.10 mmol) of TMSOTf and the reaction mixture was allowed to stir for 15 min at which time it was poured into a two-phase mixture of ethyl acetate (50 mL) and saturated aq. NaHCO3 (7 mL). The organic phase was washed with two 25 -mL portions of brine, dried (MgSO4), and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (30 cm x 3 cm). Elution with 4:1 ethyl acetate-hexanes afforded 30 as a colorless foam: yield 33 mg (66%); silica gel TLC R/ 0.30 (4:1 ethyl acetate-hexanes); 1H NMR (CDCl3) delta 2.03 (s, 6H), 2.07 (s, 3H), 2.09 (s, 3H), 2.11 (s, 3H), 2.12 (s, 3H), 3.40-3.68 (m, 8H), 3.83 (m, IH), 3.96 (m, IH), 4.05 (m, 4H), 4.25 (m, IH), 4.46 (m, IH), 4.69 (s, IH), 4.91 (m, IH), 5.00-5.25 (m, 8H), 5.61 (m, IH), and 7.34 (m, 5H); 13C NMR (CDCl3) delta 20.63, 20.70, 20.82, 29.65, 40.88, 62.08, 62.46, 63.70, 65.54, 66.07, 66.57, 67.63, 68.55, 69.15, 69.61, 69.68, 70.04, 70.30, 70.63, 96.98, 97.08, 128.07, 128.17, 128.45, 136.53, 156.48, 169.35, 169.54, 169.81, and 170.53.

Reference： [1]Patent: WO2011/19419,2011,A1 .Location in patent: Page/Page column 61

20
[ 98-59-9 ]
[ 145881-74-9 ]
[ 144208-62-8 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 4745 - 4747

21
[ 145881-74-9 ]
[ 1306601-26-2 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 4745 - 4747

22
[ 145881-74-9 ]
C₂₀H₃₀N₂O₉ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5787 - 5792

23
[ 145881-74-9 ]
[ 3068-34-6 ]
[ 1332847-06-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5787 - 5792

24
[ 6294-17-3 ]
[ 145881-74-9 ]
[ 1334953-41-1 ]

Yield	Reaction Conditions	Operation in experiment
60%		CBZ Protected Haloalkane (S2) [0096] CBZ-protected amino-ethoxyethanol (1.505 g, 6.3 mmol) was stirred vigorously with 40% KOH in water (4.67 mL, 31.5 mmol) and 100 muL tertbutlyammonium hydroxide 40% in water for 1 hour. 1-bromo-6-chlorohexane (4.41 mL, 31.5 mmol) was added all at once and the reaction was allowed to proceed overnight. The product was extracted into ethyl acetate, washed with water and brine, and purified by silica column chromatography (40% ethyl acetate in hexanes). (60% yield) [0097] M/Z calculated: 357.17, observed: 380.0 [M+Na]+ [0098] 1H NMR (500 MHz, CDCl3) 1.34 (p, 2H), 1.41 (p, 2H), 1.58 (p, 2H), 1.74 (p 2H), 3.39 (q, 2H), 3.44 (t, 2H), 3.49 (t, 2H), 3.55 (m, 4H), 3.59 (m, 2H), 5.09 (s, 2H), 5.43 (bs, 1H), 7.34 (m, 5H) 13C NMR (125 MHz, CDCl3) 25.25, 26.61, 29.36, 40.79, 45.02, 66.56, 69.96, 70.22, 71.22, 128.02, 128.03, 128.44, 136.58, 156.45

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 16346 - 16349
[2]Patent: US2013/302258,2013,A1 .Location in patent: Paragraph 0095; 0096; 0097; 0098

25
[ 91-01-0 ]
[ 145881-74-9 ]
[ 1370285-80-5 ]

Yield	Reaction Conditions	Operation in experiment
46%	With triethylamine methanesulfonic acid; at 80℃; for 0.166667h;Microwave irradiation;	General procedure: alcohol (0.1 mL) was added to a microwave vial charged with DPM-OH (1) (100 mg, 0.54 mmol) and a stirrer bar. To this suspension was added pIL (0.25 mL) and the reaction heated to the desired temperature under microwave irradiation. Once complete the contents of the vial cooled and diluted with diethylether (2 mL) and filtered under vacuum through a silica plug. The microwave vial and silica plug were thoroughly washed with Et2O. The filtrate was then collected and solvent removed in vacuo to give clear oil.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 2035 - 2039

26
[ 145881-74-9 ]
[ 1299292-02-6 ]

Reference： [1]Patent: WO2011/53614,2011,A1

27
[ 145881-74-9 ]
[ 3006-60-8 ]
[ 1261568-35-7 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluorormethanesulfonic acid; In dichloromethane; at 20℃;Inert atmosphere; Reflux;	In a 12 L flask was placed 2 (440 g, 1130 mmol), 4 (297 g, 1243 mmol, LI eq.), and anhydrous DCM (4.4 L, 10 vols) under nitrogen atmosphere. The mixture was added trifluoromethanesulfonic acid (TfOH, 17.3 g, 1 .2 mL, 113 mmol, 0.1 eq.) via a syringe at RT, and then the resulting mixture was warmed to a gentle reflux. After 18 hr, LC showed the reaction was not complete. Additional TfOH (5.1 mL, 0.05 eq.) was introduced via a syringe, and the mixture was refluxed further. After 9 hr, the reflux condenser was replaced with a distillation head, and the mixture was concentrated to about half of the original volume under vacuum-. The resulting DCM- solution was washed successively with aqueous solution of 2CO3 (10 wt%, 780 mL), water (1.0 L), andNaCl solution (20 wt%5 0.75-L), and then dried over anhydrous MgS04. After filtration, the filtrate -was placed" in a 12 L flask, and the solvent was switched to 2-Me-THF by distillation of DCM with addition of 2-Me-THF until the final volume was ca. 2.64 L, and the residual DCM was below 5% judged ?y 1H-NMR. White solid" precipitated slowly during the solvent switch. The resulting slurry was added heptane (Gamma320 mL, 3 vols) slowly over 1 hr maintaining the internal temperature at 35C. After the addition was completed, the -slurry was stirred at the same temperature for 1 hr then allowed to cool to RT slowly. The solid was collected by filtration, washed with 2-Me-THE/heptane (5/3, v/v, 2.0 L, 4.5 vols), and -dried under vacuum with N2 sweep affording 5 as a white microcrystalline solid (514 g, 1130 mmol).

Reference： [1]Patent: WO2011/53614,2011,A1 .Location in patent: Page/Page column 8-10

28
3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranosyl diphenyl phosphate [ No CAS ]
[ 145881-74-9 ]
[ 1266609-55-5 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 2883 - 2886

29
[ 145881-74-9 ]
[ 4163-65-9 ]
[ 1433192-30-3 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 5259 - 5262

30
[ 145881-74-9 ]
[ 4163-60-4 ]
[ 1433192-31-4 ]

Yield	Reaction Conditions	Operation in experiment
76.97%	With boron trifluoride diethyl etherate; In dichloromethane; at 20℃;Cooling with ice;	(2) Dissolve 12.3 g of compound 2 and 12.02 g of beta-D-galactose pentaacetate in 150 mL of dichloromethane, and slowly add 7.64 mL of boron trifluoride diethyl ether under ice bath conditions, and stir overnight at room temperature. Then, it was quenched by adding water and saturated sodium bicarbonate, and extracted with dichloromethane. EA: PE = 1: 5 was passed through the column to obtain 13.5 g of compound 3 with a yield of 76.97%.

Reference： [1]Patent: CN110372765,2019,A .Location in patent: Paragraph 0047; 0050-0051
[2]Chemistry - A European Journal,2013,vol. 19,p. 5259 - 5262

31
2,3,4-tri-O-acetyl-α/β-L-fucopyranosyl trichloroacetimidate [ No CAS ]
[ 145881-74-9 ]
benzyl 2-(2-(2,3,4-tri-O-acetyl-α-L-fucopyranosyloxy)ethoxy)ethylcarbamate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 5259 - 5262

32
3,4,6-tetra-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-O-(carbamoyl)-α-D-mannopyranosyl)-β-L-gulopyranosyl diphenylphosphate [ No CAS ]
[ 145881-74-9 ]
2-[2-(benzyloxycarbonylamino)ethyloxy]ethyl 3,4,6-tri-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-O-(carbamoyl)-α-D-mannopyranosyl)-α,β-L-gulopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	(02551 3 ,6-Tri- -acetyI-2- -(3^6-tri- -acei> -2- -(carbantoyI}--D- mannopyranosyl)-tt,p~L-gulopyranosyl Benzyl 2~(2-Eihoxy)ethyleaf hamate (55). To a stiffed solution containing 31.0 mg (0.04 mmol) of phosphate ester 52 in 3.9 mL of anh dichlorometh.ane was added a solution of 9.40 mg (0.04 mmol) of CBz linker 54 in 4.5 mL of anh dichlororaethane at 0 C. To the cooled reaction mixture was then added 41 ,0 uL (51 ,0 mg, 0,23 mmol) of TMSOTf and the reaction mixture was stirred at 0 C fo 15 min at which time it was poured into a mixture of 20 mL of ethyl acetate and 20 mL of said aq aHCO;;. The aqueous and organic layers were separated and the organic layer was washed with three 10-mL portions of water and brine, and then dried. (MgSO*). The solvent was concentrated under diminished pressure to afford a erode residue. The residue was applied to a silica gel column (12 x 2 cm). Elution with 3: 1 ethyl acetate~-hexan.es afforded disaechaiide-Uiiker conjugate 55 as a colorless oil: yield 12 nig (39 %): silica gel TLC % 0.12 (3: 1 ethyi acetate-hexanes); fH NMR. (CDCi3) 5 1.99 (s, 3H), 2.02 (s, 2H), 2.04 (s, 3H), 2.07 (s, 3H), 2.09 <s, 3H), 2. 1.2 (s, 3H), 3.37-3.42 (ms 2H), 3.55- 3.65 (.m, 3H), 3.67-3.69 (m, 2H), 3.83-3.88 fm, 1H), 3.97 (t 1H, J = 3.9 Hz), 4.03- 4.09 (m, 2H), 4.10-4.15 (m, 1H), 4.28 (dd, 1H, J- 1 1.9, 5.2 Hz), 4.46 (t, 1H, J = 6.6 Hz), 4.77-4.90 (or s. 2H), 4.93 (d, J - 3.9 Hz, 1H), 5.03-5.06 (m, 3E 5.09 (s, 2H), 5.23-5.29 (m, 3H), 5.46-5.48 (m, 1H), 7.28-7.37 fm, 5H); ' NMR (CDCb) delta 20.62, 20.65, 20.72, 20.76, 40,9, 62.1 , 62.5, 63.8, 65,8, 66.1, 66.6, 67.6, 68.6, 68.7, 69.0, 70.07, 70.16, 79.3, 7] .0, 77.2, 97.0, 97.6, 128.10, 128.18, 128.5, 136.5, 155.0. 169.3, 169.72, 169.73, 170.0, 1 70.56, 170.59; mass spectrum (APCI), mfz 859.2987 (M + Hf (
39%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	To a stirred solution containing 31.0 mg (0.04 mmol) of phosphate ester 37 in 3.9 mL of anh dichloromethane was added a solution of 9.40 mg (0.04 mmol) of CBz linker 39 in 4.5 mL of anh dichloromethane at 0 C. To the cooled reaction mixture was then added 41.0 tL (51.0 mg, 0.23 mmol) of TMSOTf and the reaction mixture was stirred at 0 C for 15 mm at which time it was poured into a mixture of 20 mL of ethyl acetate and 20 mL of satd aq NaHCO3. The aqueous and organic layers were separated and the organic layer was washed with three 1 0-mL portions of water and brine, and then dried (MgSO4). The solvent was concentrated under diminished pressure to afford a crude residue. The residue was applied to a silica gel colunm (12 x 2 cm). Elution with 3:1 ethyl acetate-hexanes afforded disaccharide-linker conjugate 40 as a colorless oil: yield 12 mg (39 %); silica gel TLC R0.12 (3:1 ethyl acetate-hexanes); ?HNMR (CDC13) oe 1.99 (s, 3H), 2.02 (s, 2H), 2.04 (s, 3H), 2.07 (s, 3H), 2.09 (s, 3H), 2.12 (s, 3H), 3.37-3.42 (m, 2H), 3.55-3.65 (m, 3H), 3.67-3.69 (m, 2H), 3.83-3.88 (m, 1H), 3.97 (t, 1H, J= 3.9 Hz), 4.03-4.09 (m, 2H), 4.10-4.15 (m, 1H), 4.28 (dd, 1H,J= 11.9, 5.2 Hz), 4.46 (t, 1H,J=6.6 Hz), 4.77-4.90 (br s, 2H), 4.93 (d, J= 3.9 Hz, 1H), 5.03-5.06 (m, 3H), 5.09 (s, 2H), 5.23-5.29 (m, 3H), 5.46-5.48 (m, 1H), 7.28-7.37 (m, 5H); ?3C NMR (CDC13)o 20.62, 20.65, 20.72, 20.76, 40.9, 62.1, 62.5, 63.8, 65.8, 66.1, 66.6, 67.6, 68.6, 68.7, 69.0, 70.07, 70.16, 70.3, 71.0, 77.2, 97.0, 97.6, 128.10, 128.18, 128.5, 136.5,155.0, 169.3, 169.72, 169.73, 170.0, 170.56, 170.59; mass spectrum (APCI), m/z859.2987 (M + H) (C37H51N2021 requires m/z 859.2984).
39%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	To a stirred solution containing 31.0 mg (0.04 mmol) of phosphate ester 39 in 3.9mL of anh dichloromethane was added a solution of 9.40 mg(0.04 mmol) of CBz linker 41 in 4.5 mL of anh dichloromethaneat 0 C. To the cooled reaction mixture was added41.0 muL (51.0 mg, 0.23 mmol) of TMSOTf, and the reactionmixture was stirred at 0 C for 15 min, at which time it was poured into a mixture of 20 mL of ethyl acetate and 20 mL of satd aq NaHCO3. The aqueous and organic layers were separated, and the organic layer was washed successively with three 10 mL portions of water and brine and then dried(MgSO4). The solvent was concentrated under diminished pressure to afford a crude residue. The residue was applied to a silica gel column (12 × 2 cm). Elution with 3:1 ethyl acetate-hexanes afforded disaccharide-linker conjugate 42 as a colorless oil: yield 12 mg (39%); silica gel TLC Rf 0.12 (3:1ethyl acetate-hexanes); 1H NMR (CDCl3) delta 1.99 (s, 3H), 2.02(s, 3H), 2.03 (s, 3H), 2.07 (s, 3H), 2.09 (s, 3H), 2.12 (s, 3H),3.37-3.42 (m, 2H), 3.55-3.65 (m, 3H), 3.67-3.69 (m, 2H),3.83-3.88 (m, 1H), 3.97 (t, 1H, J = 3.9 Hz), 4.09-4.15 (m,4H), 4.28 (dd, 1H, J = 11.9 and 5.2 Hz), 4.46 (t, 1H, J = 6.6Hz), 4.77-4.90 (br s, 2H), 4.93 (d, 1H, J = 3.9 Hz), 5.03-5.06(m, 4H), 5.23-5.29 (m, 3H), 5.46-5.48 (m, 1H), 7.30-7.35(m, 5H); 13C NMR (CDCl3) delta 20.62, 20.65, 20.72, 20.76, 40.9,62.1, 62.5, 63.8, 65.8, 66.1, 66.6, 67.6, 68.6, 68.7, 69.0, 70.07,70.16, 70.3, 71.0, 77.2, 97.0, 97.6, 128.10, 128.18, 128.5, 136.5,155.0, 169.3, 169.72, 169.73, 170.0, 170.56, 170.59; mass spectrum (APCI), m/z 859.2987 (M + H)+ (C37H51N2O21requires m/z 859.2984).

Reference： [1]Patent: WO2014/145109,2014,A1 .Location in patent: Paragraph 0255
[2]Patent: WO2014/152718,2014,A1 .Location in patent: Paragraph 0237; 0248
[3]Biochemistry,2014,vol. 53,p. 6800 - 6810

33
3,4,6-tri-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-O-(N-methylcarbamoyl)-α-D-mannopyranosyl)-β-L-gulopyranosyl diphenyl phosphate [ No CAS ]
[ 145881-74-9 ]
2-[2-(benzyloxycarbonylamino)ethyloxy]ethyl 3,4,6-tri-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-O-(N-methylcarbamoyl)-α-D-mannopyranosyl)-α,β-L-gulopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	[02561 3,4,6-Tri-i -a?eiyl-2- -(3^6~tri-i -acety~2~ -(methykar D-iaiii}Opyrai}Os 1)-a,p-L-guopyranos l Benzyl 2-(2-Etfooxy)ethyiearbamate (56). To a stirred solution containing 90,0 mg (0.10 mmol) of phosphate ester 53 in 1 .1 rnL of anh dichloromelhane was added a solution of 22.0 mg (0,09 mmol) of CBz linker 54 in 1 .1 ml, of anh dichbromethane at 0 CC. To the cooled reaction mixture was then added 33,0 muL· (41 ,0 mg, 0, 18 mmol) of MSOTf and the reaction mixture was stirred at 0 V'C for 15 min at which time it was poured into a mixture of 20 nil, of ethyl acetate and 20 rnL of said aq NaHCOj. The aqueous and organic layers were separated and the organic layer was washed with three lO-jiiL portions of water and brine, then dried (MgSO*). The solvent was concentrated under diminished pressure to afford a crude residue. The residue was applied iotaomicron a silica gel column (25 x 3 cm). Elation with 12: 12 1 ethyi acetate - hexanes -methanol afforded disaccharide -linker conjugate 56 as a colorless oil: yield 56 mg (63%); silica gel TLC R{ 0.20 (12: 12: i ethyl acetate~xaties~raethano1); NMR iCDC ) 1.96 (s, 3H), 2.00 (s, 3H), 2.01 (a, 3M), 2.05-2.08 <m, 6H), 2.10 (s, 3H)5 2.78 (d, 31 J- 4.6 Hz), 3.38 (d, 2H, J==== 4.4 Hz), 3.51-3.70 (m, 4H), 3.78-3.87 (ra, H), 3.95 (d, .1H, 3.5 Hz), 4.00-4.15 (m, 4H), 4,20-4.30 (m, 2H), 4.45 it, 1H, J = 6, 1 Hz), 4.89-5.12 (m, 6H), 5.20-5.30 (ra, 3H), 5.42-5.49 (m, 1H), 5.46 (s, 1H) and 7.27-7.38 (m, 5H); i 5C NMR (CDC ) 520.7.1 , 20.73, 20.77, 20.80, 20.84, 20.88, 27.7, 62.3, 62.7, 63.9, 66.0, 66.3, 66.7, 68.7, 68.9, 69.2, 70.1 , 70.2, 70.4, 97.2, 97,9, 128.21 , 128.23, 128.28, 128.59, 128.61, 136.7, 155.5, 169.4, 169.80, 169.84, 170.0, 170.66 and 170.69; HRM'S (APCI), m z 873.3166 (M + if { AN.Gjs requires m/z 873.3141 ).
63%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	To a stirred solution containing 90.0 mg (0.10 mmol) of phosphate ester 38 in 1.1 mL of anh dichloromethane was added a solution of 22.0mg (0.09 mmol) of CBz linker 39 in 1.1 mL of anh dichloromethane at 0 C. To the cooled reaction mixture was then added 33.0 tL (41.0 mg, 0.18 mmol) of TMSOTf and the reaction mixture was stirred at 0 C for 15 mm at which time it was poured into a mixture of 20 mL of ethyl acetate and 20 mL of satd aq NaHCO3. The aqueous and organic layers were separated and the organic layer was washed with three 1 0-mL portions of water and brine and then dried (MgSO4). The solvent was concentrated under diminished pressure to afford a crude residue. The residue was applied to a silica gel column (25 x 3 cm). Elution with 12:12:1 ethyl acetate-hexanes-methanol afforded disaccharide-linker conjugate 41 as a colorless oil: yield 56 mg (63%); silica gel TLC Rf 0.20 (12:12:1 ethyl acetate-hexanes-methanol); ?HNMR (CDC13) oe 1.96 (s, 3H), 2.00 (s, 3H), 2.01 (s, 3H), 2.05-2.08 (m, 6H), 2.10 (s, 3H), 2.78 (d, 3H, J= 4.6 Hz), 3.38 (d, 2H, J 4.4 Hz), 3.51-3.70 (m, 4H), 3.78-3.87 (m, 1H), 3.95 (d, 1H,J 3.5 Hz), 4.00-4.15 (m, 4H), 4.20-4.30 (m, 2H), 4.45 (t, 1H, J= 6.1 Hz), 4.89-5.12 (m, 6H), 5.20-5.30 (m, 3H), 5.42-5.49 (m, 1H), 5.46 (s, 1H) and 7.27-7.3 8 (m, 5H); ?3C NMR (CDC13) oe20.71, 20.73, 20.77, 20.80, 20.84, 20.88, 27.7, 62.3, 62.7, 63.9, 66.0, 66.3, 66.7, 68.7, 68.9, 69.2, 70.1, 70.2, 70.4, 97.2, 97.9, 128.21, 128.23, 128.28, 128.59,128.61, 136.7, 155.5, 169.4, 169.80, 169.84, 170.0, 170.66 and 170.69; HRMS (APCI), m/z 873.3166 (M + H) (C38H53N2021 requires m/z 873.3141).
63%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	To a stirred solution containing 90.0 mg (0.10 mmol) of phosphate ester 40 in 1.1 mL of anh dichloromethane was added a solution of 22.0 mg (0.09 mmol) of CBz linker 41 in 1.1 mL of anh dichloromethane at 0 C. To the cooled reaction mixture was added 33.0 muL (41.0 mg, 0.18 mmol) of TMSOTf, and the reaction mixture was stirred at 0 C for 15 min, at which time it was poured into a mixture of 20 mL of ethyl acetate and 20 mL of satd aq NaHCO3. The aqueous and organic layers wereseparated, and the organic layer was washed with three 10 mLportions of water and brine and then dried (MgSO4). Thesolvent was concentrated under diminished pressure to afford acrude residue. The residue was applied to a silica gel column(25 × 3 cm). Elution with 12:12:1 ethyl acetate-hexanes-methanol afforded disaccharide-linker conjugate 43 as acolorless oil: yield 56 mg (63%); silica gel TLC Rf 0.20(12:12:1 ethyl acetate-hexanes-methanol); 1H NMR (CDCl3) delta 1.96 (s, 3H), 2.00 (s, 3H), 2.01 (s, 3H), 2.05-2.08 (m, 6H), 2.10 (s, 3H), 2.78 (d, 3H, J = 4.6 Hz), 3.38 (d,2H, J = 4.4 Hz), 3.51-3.70 (m, 4H), 3.78-3.87 (m, 1H), 3.95(d, 1H, J = 3.50 Hz), 4.00-4.15 (m, 4H), 4.20-4.30 (m, 2H),4.45 (t, 1H, J = 6.1 Hz), 4.89-5.12 (m, 6H), 5.20-5.30 (m,3H), 5.42-5.49 (m, 1H), 5.46 (s, 1H), 7.27-7.38 (m, 5H); 13CNMR (CDCl3) delta 20.71, 20.73, 20.77, 20.80, 20.84, 20.88, 27.7,62.3, 62.7, 63.9, 66.0, 66.3, 66.7, 68.7, 68.9, 69.2, 70.1, 70.2,70.4, 97.2, 97.9, 128.21, 128.23, 128.28, 128.59, 128.61, 136.7,155.5, 169.4, 169.80, 169.84, 170.0, 170.66, 170.69; massspectrum (APCI), m/z 873.3166 (M + H)+ (C38H53N2O21requires m/z 873.3141).

Reference： [1]Patent: WO2014/145109,2014,A1 .Location in patent: Paragraph 0256
[2]Patent: WO2014/152718,2014,A1 .Location in patent: Paragraph 0237; 0249
[3]Biochemistry,2014,vol. 53,p. 6800 - 6810

34
[ 145881-74-9 ]
3-O-(carbamoyl)-α-D-mannopyranosyl benzyl 2-(2-ethoxy)ethylcarbamate [ No CAS ]

Reference： [1]Patent: WO2014/145109,2014,A1
[2]Patent: WO2014/152718,2014,A1

35
[ 145881-74-9 ]
α-D-mannopyranosyl benzyl 2-(2-ethoxy)ethylcarbamate [ No CAS ]

Reference： [1]Patent: WO2014/145109,2014,A1
[2]Patent: WO2014/152718,2014,A1

36
3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-(methylcarbamoyl)-α-D-mannopyranosyl)-β-L-gulopyranosyl diphenyl phosphate [ No CAS ]
[ 145881-74-9 ]
3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-(methylcarbamoyl)-α-D-mannopyranosyl)-α,β-L-gulopyranosyl benzyl 2-(2-ethoxy)ethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	{0267j 3 ,6-Tri- -acetyI-2- -(2^6- i- -acei> -3-f -(methykarbai0yi)-- D-rfiaii pyraii sy)~a.,p~L-gopyraiH)sy Benzyl 2-(2-Eihoxy)ethykarbaniate (63). To a stirred solution containing 44 nig (50 praol) of the phosphate ester 62 in 0.6 mL of anh dichloromethane was added a solution of 1 1 rag (40 mukappa>1) of the CBz-protecied Sinker 54 in 0,6 mL of anh dichloromethane at 0 C. To the cooled reaction mixture was added 16 jiL (20 mg, 90 mutauetaomicron) of TMSOTf and the reaction mixture was stirred at 0 C for 15 rain. The reaction mixture was poured into a mixture of 10 mL ethyl acetate and 10 mL said aq NaHC<. The organic and aqueous layers were separated and the organic layer was washed with three 10-mL portions of water and brine and then dried (MgS<). The organic layer was concentrated under diminished pressure to afford a cntde residue. 'T he residue was applied to a silica gel column (25 chi 3 cm). Elation with 12: 12: 1 ethyl acetate-hexanes-raeihanol afforded linker conjugate 63 as a colorless oil. The product was isolated as a (5:3) mixture of anomers: yield 32 mg (73%); silica gel TLC i/ .1 1 ( 12: 12: 1 ethyl acetate-hexarjes-methanol); 'H NM'R (CDCl. (major anoraer) 3 2.03 (s, 3E), 2.05 (s, 3H), 2.06-2.15 (in, J2H), 2.71 (d, 3H, J~ 4.8 Ez), 3.40 (s, .Hi), 3.51-3.74 (m, 6H), 3.79-3.89 (ra, 1 H), 3.92-4.01 (m, 1H), 3.99-4.21 (m, 4H), 4.21 -4.41 (m, 2H), 4.55-4.63 (m, 2H), 4.89-5.04 (m, 211), 5.09 (d, 2H, J:~ 5.6 Hz), 5.12-5.30 (m, 3H), 5.32-5.41 (m, 1H), 5.65-5.73 (m, 1 H) and 7.27-7.39 (m, 5H); UC MR (CDCL) delta 20.78, 20.83, 20.87, 20.91 , 20.93, 20.98, 21.0, 27.67, 27.69, 40.9, 41.1. 53.6, 61.8, 61.9, 62.3, 62.7, 63.9, 65.6, 65.7, 66.1, 66.4, 66.7, 67.9, 68.0, 68.6, 68.8, 69.0, 69.3, 69.5, 69.72, 69.76. 70.0, 70.1 , 70.3, 70.4, 70.52, 70.55, 70.7, 72.3, 97.1, 97.2, 120.38, 120.43, 128.2, 128.3, 128.60, 128.65, 129.8, 130.0, 136.8, 155.7. 156.7, 169.33, 169.37, 169.39, 169.47, 169.54, 169.6, 170.0, 170.5, 170.6, .170.7, 170.8 and 170.9; mass spectrum (APCI), m/z 873.3150 (M + H) (C3S.H53 2O21 requires 873.3141).
73%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	To a stirred solution containing 44 mg (50 imo1) of the phosphate ester 50 in 0.6 mL of anh dichloromethane was added a solution of 11 mg (40 imol) of the CBz-protected linker 39 in 0.6 mL of anh dichloromethane at 0 C. To the cooled reaction mixture was added 16 tL (20 mg, 90 imol) of TMSOTf and the reaction mixture was stirred at 0 C for 15 mm. The reaction mixture was poured into a mixture of 10 mL ethyl acetate and 10 mL satd aq NaHCO3. The organic and aqueous layers were separated and the organic layer was washed with three 1 0-mL portions of water and brine and then dried (MgSO4). The organic layer was concentrated under diminished pressure to afford a crude residue. The residue was applied to a silica gel column (25 x 3 cm). Elution with 12:12:1 ethyl acetate-hexanes-methanol afforded linker conjugate 51 as a colorless oil. The product was isolated as a (5:3) mixture of anomers: yield 32 mg (73%); silica gel TLC Rf 0.11(12:12:1 ethyl acetate-hexanes-methanol); ?H NMR (CDC13) (major anomer) oe 2.03 (s, 3H), 2.05 (s, 3H), 2.06-2.15 (m, 12H), 2.71 (d, 3H, J 4.8 Hz), 3.40 (s, 1H), 3.51-3.74 (m, 6H), 3.79-3.89 (m, 1H), 3.92-4.01 (m, 1H), 3.99-4.21 (m, 4H), 4.21-4.41 (m, 2H), 4.55-4.63 (m, 2H), 4.89-5.04 (m, 2H), 5.09 (d, 2H, J 5.6 Hz), 5.12-5.30 (m, 3H), 5.32-5.41 (m, 1H), 5.65-5.73 (m, 1H) and 7.27-7.39(m, 5H); ?3C NMR (CDC13) oe 20.78, 20.83, 20.87, 20.91, 20.93, 20.98, 21.0,27.67, 27.69, 40.9, 41.1, 53.6, 61.8, 61.9, 62.3, 62.7, 63.9, 65.6, 65.7, 66.1, 66.4,66.7, 67.9, 68.0, 68.6, 68.8, 69.0, 69.3, 69.5, 69.72, 69.76, 70.0, 70.1, 70.3, 70.4,70.52, 70.55, 70.7, 72.3, 97.1, 97.2, 120.38, 120.43, 128.2, 128.3, 128.60, 128.65,129.8, 130.0, 136.8, 155.7, 156.7, 169.33, 169.37, 169.39, 169.47, 169.54, 169.6,170.0, 170.5, 170.6, 170.7, 170.8 and 170.9; mass spectrum (APCI), m/z 873.3150(M + H) (C38H53N2021 requires 873.3141).

Reference： [1]Patent: WO2014/145109,2014,A1 .Location in patent: Paragraph 0267
[2]Patent: WO2014/152718,2014,A1 .Location in patent: Paragraph 0256; 0263

37
3,4,6-tetra-O-acetyl-2-O-(2,3,6-tri-O-acetyl-4-O-(carbamoyl)-α-D-mannopyranosyl)-β-L-gulopyranosyl diphenylphosphate [ No CAS ]
[ 145881-74-9 ]
3,4,6-tetra-O-acetyl-2-O-(2,3,6-tri-O-acetyl-4-O-(carbamoyl)-α-D-mannopyranosyl)-α,β-L-gulopyranosyl benzyl 2-(2-ethoxy)ethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	0274\| 3 ,6-Tri- -acetyI-2- -(2,3,6-tri- -acet 4-4- -(carbatnoyI}--D- iiiatmopyranosyl)~,{i~L-gukipyraiiosyf Benzyl 2~(2-Ethoxy)ethyicarbainate (67), To a stirred solution containing 27,0 rag (0.03 mmol) of phosphate ester 66 in 3.9 mL of anii dichloromethane was added a solution of 8.20 mg (0.03 mmol) of CBz-proieeied Sinker 54 in 3.9 mL of aab dichloromethane at 0 C. To the cooled reaction mixture was then added 8.20 mu,. (10,1 mg, 0.04 mmol) of T SOTf, The reaction mixture was stirred at.0 C for 15 mrn and then poured into a mixture of 20 mL of ethyl acetate and 4 mL of said aq NaHCOj. The aqueous and. organic layers were separated and the organic layer was washed with three 10-mL portions of water and brine and then dried (MgSO. - The solvent was concentrated under diminished pressure to afford a crude residue. 'Hie residue was applied to a silica gel column (12 x 2 cm). Ehuion with 3:1 ethyl acetate-hexanes afforded 67 as a colorless oil. The product, isolated as a mixture of anomers: yield 7 mg (26%); silica gel TJX Rf OA 1 (4:1 ethyl acetate-hexanes ; H NMR (CDCl?) 6 1 ,99 (s, 3H), 2.04 is, mi 2.09 (s, 3H), 2.10 (s, 3H), 2.12 (s, 3H), 2.13 (s, 3H), 3.33-3.45 (br s, 2H), 3.56-3.65 (m, 211), 3.67-3.73 (ra, 2H), 3.82-3.88 (m, 1H), 3.96 (t, 1 H, J = 4.0 Hz), 4.03-4.11 (m, 3H), 4.12-4.19 (m, 2M), 4.30 (dd, IE., J - 12.0, 5.7 Hz), 4.42 (t, 1H, J= 6.5 Hz), 4.93-4,98 (m, 3H), 5.00-5.03 (m( 1 H), 5.07 (s, 2H 5.12- 5.17 (m, 2H), 5.24-5.30 (m, 3H), 7.30-7.36 (m, 5H); l3C NMR (CDQj) 20.81 , 20.89, 20.90, 20.93, 21.0, 29.8, 41 .2, 62.3, 62.9, 63.8, 65.7, 67.0, 67. 1, 68.1 , 68.69, 68.72, 69.6, 70. i , 71.1 , 77.5, 97.2, 97.6, 128,32, 128,38, 128.7, 136.5, 155.5, 156.9, 169.5, 169.8, 1 9.9, 170,2, 170.7, 170,8; mass spectrum (APCI), mz 859.2975 (M -f Hf (Cntibi jCta requires mlz 859.2984).
26%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	To a stirred solution containing 27.0 mg (0.03 mmol) of phosphate ester 55 in 3.9 mL of anh dichloromethane was added a solution of 8.20mg (0.03 mmol) of CBz-protected linker 39 in 3.9 mL of anh dichloromethane at 0 C. To the cooled reaction mixture was then added 8.20 tL (10.1 mg, 0.04 mmol) of TMSOTf. The reaction mixture was stirred at 0 C for 15 mm and then poured into a mixture of 20 mL of ethyl acetate and 4 mL of satd aq NaHCO3. The aqueous and organic layers were separated and the organic layer was washed with three 1 0-mL portions of water and brine and then dried (MgSO4). The solvent was concentrated under diminished pressure to afford a crude residue. The residue was applied to a silica gel colunm (12 x 2 cm). Elution with 3:1 ethyl acetate-hexanes afforded 56 as a colorless oil. The product isolated as a mixture of anomers: yield 7 mg (26%); silica gel TLC Rf 0.11(4:1 ethyl acetate-hexanes); ?H NMR (CDC13) oe 1.99 (s, 3H), 2.04 (s, 3H), 2.09 (s, 3H), 2.10 (s, 3H), 2.12 (s, 3H), 2.13 (s, 3H), 3.33-3.45 (br s, 2H), 3.56-3.65 (m, 2H), 3.67-3.73 (m, 2H), 3.82-3.88 (m, 1H), 3.96 (t, 1H, J = 4.0 Hz), 4.03-4.11 (m, 3H), 4.12-4.19 (m, 2H), 4.30 (dd, 1H,J= 12.0, 5.7 Hz), 4.42 (t, 1H, J= 6.5 Hz), 4.93-4.98 (m, 3H), 5.00-5.03 (m, 1H), 5.07 (s, 2H), 5.12-5.17 (m, 2H), 5.24-5.30 (m, 3H), 7.30-7.36 (m, 5H); ?3C NMR (CDC13) 20.81,20.89, 20.90, 20.93, 21.0, 29.8, 41.2, 62.3, 62.9, 63.8, 65.7, 67.0, 67.1, 68.1, 68.69,68.72, 69.6, 70.1, 71.1, 77.5, 97.2, 97.6, 128.32, 128.38, 128.7, 136.5, 155.5,156.9, 169.5, 169.8, 169.9, 170.2, 170.7, 170.8; mass spectrum (APCI), m/z859.2975 (M + H) (C37H5,N202, requires m/z 859.2984).

Reference： [1]Patent: WO2014/145109,2014,A1 .Location in patent: Paragraph 0274
[2]Patent: WO2014/152718,2014,A1 .Location in patent: Paragraph 0267; 0270

38
3,4,6-tetra-O-acetyl-2-O-(2,3,6-tri-O-acetyl-4-O-(methylcarbamoyl)-α-D-mannopyranosyl)-β-L-gulopyranosyl diphenylphosphate [ No CAS ]
[ 145881-74-9 ]
3,4,6-tri-O-acetyl-2-O-(2,3,6-tri-O-acetyl-4-O-(methylcarbamoyl)-α-D-mannopyranosyl)-α,β-L-gulopyranosyl benzyl 2-(2-ethoxy)ethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	{02811 3A6-Tri-0-acetyl-2-i -^^^ D-maii pyraii sy)~a.,p~L-gopyraiH)sy Benzyl 2^2-Ethoxy)er.hyJcarbamate (72). To a stirred solution containing 38. mg (0.04 mmol) of phosphate ester 71 in 0.5 raL of anii dichioromethane was added a solution of 10.0 mg {0.04 mmol) of CBz-proieeied Sinker 54 in 0,5 mL of anh dichioromethane at 0 C. To the cooled reaction mixture was then added 14.0 mu, (17.0 mg, 0.08 mmol) of TMSOTf. The reaction mixture was stirred at 0 C for 15 min and then poured into a mixture of 20 mL of ethy l acetate and 20 mL of satd aq NaHCOj. The aqueous and organic layers were separated and the organic layer was washed with three 10-m.L portions of water and brine and then dried (MgSOj). The solvent was concentrated under diminished pressure to afford a crude residue. The residue was applied to a silica gel column (25 x 3 cm). Etation with 12: 12:1 ethyl aceta-e-hexanes-methanol afforded 72 as a coiorless oil. The product isolated as a mixture of anomers: yield 19 mg (51%); silica gel TLC Rf0.l4 (12: 12: 1 ethyl acetate~hexaoe~melhanol); lH NMR (CDCb) delta .92-2. I 4 (m, 1 8H), 2.71 (t, 3H, - 4A Hz), 3.40 id, 3H, J = 4.9 Hz), 3.52-3.77 (ra, 8H), 3.85 (ddJ B, </= 8.4 and 3.2 Hz), 3.95 it 1 H, J = 3.9 Hz), 4.27 (dd, 21·, J~~ 13.4 and 7.3 Hz), 4.40 (t, 1 H, J ::: 6.4 Hz), 4.88-5.04 (m, 3H), 5.05-5.22 (m, 6H), 5.25 (dd, 1 H, J = 7.3 and 3.6 Hz) and 7.28-7.40 (m, 5H); NMR (CDC1. delta 20.78, 20.83 20.85, 20.87, 20.92, 20,95, 27.7, 61.9, 62.3, 63.1 , 63.8, 65.7, 66.8, 66,9, 68.1 , 68.7, 68.8, 69.6, 69,8, 70.2, 71.0, 72.3, 7,2, 97.5, 128.27, 128.33, 128.65, 128.67, 169.5, 169.7, 169.8, 169.9, 170.57, 170.63 and 170.7; HRMS (APCI), m/z 873.3142 (M + H)" (CjH53 202j requires m z 873.3141 ).

Reference： [1]Patent: WO2014/145109,2014,A1 .Location in patent: Paragraph 0281

39
3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-altropyranosyl)-β-L-gulopyranosyl diphenylphosphate [ No CAS ]
[ 145881-74-9 ]
3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-altropyranosyl)-β-L-gulopyranosyl benzyl 2-(2-ethoxy)ethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	}0292\| ,4 )-i'n-f -acetyJ-2- -(2,4,6-'rri-6^acetyI-3- arbainovl--0- aitropyranosyl)-^-L-gutopyranosyl Benzyl 2-(2-Ettioxy)ethykarbaiate (81). To a stirred solution containing 31 mg (40 muetaiotaomicronIota) of phosphate ester 79 in 0.45 ml of anh dichlororaethane was added a solution of 8,0 mg (30 mupiiotaomicron) of CBz- protected linker 54 in 0.45 raL of anh dichloromethane at 0 C. To the reaction mixture was added 12 uJL (15 rag, 80 umol) of TMSOTf and the reaction mixture was stirred at 0 C for 15 min. The reaction mixture was poured into a mixture of 1 niL of ethyl acetate and 10 raL said aq NaHCQ,. The a ueous and organic layers were separated and the organic layer was washed with three 10-niL portions of water and brine and then dried (MgSO.j)- The solvent was concentrated under diminished pressure to afford a crude residue. The residue was applied to a silica, gel column (25 x 2 cm). Eution with 12:12:1 ethyl acetate-hexanes-methanol afforded 81 as a colorless oil: yield 15 mg (48%): silica gel TLC . 0.17 (11:1 1:1 ethyl acetate-hexanes-methanol); lH NMR (OX) 3 iH NMR (CDC) delta 1 .95- 2.07 (m, 6.R), 2.07-2.15 (m, 12H), 3.4 (t, 2.H,J - 9,5 Hz), 3.59 (d, 2R ./- 5,0 Hz), 3.61-3.71 (m, 3H), 3.87 (di, iH, J= 12.8 and 6.5 Hz), 3.94-4.04 (m, IH), 4.04-4.20 (m, 3H), 4.2 -4,26 (ms I H), 4.36-4.48 (m, IH), 4.49-4.60 (m, 1H), 4.75 (d 1 H, J FontWeight="Bold" FontSize="10" 7.5 Hz), 4.84-5.05 (m, 411), 5.05-5.20 (m, 4H), 5.21-5.29 (ffl, I H), 5.32- 5.49 (m, 2tt) and 7.27-7.38 (m, 5H) ; C NMR (CDC ) delta 20.75, 20.77, 20.82, 20.85, 20.88, 20.92, 0.9, 62.1, 62.3, 62.6, 65.1, 65.2, 66.9, 67.8, 68.1, 68.5, 68.6, 69.2, 70.37, 70.45, 99.5, 128.3, 128.4, 128.5, 128.7, 136.6, 155.7, 169.0, 169.4, 169.61. 169.65, 170.6, 170.82 and 170.89: HRMS (APC), m/z 859.2973 (M + Hf
48%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	To a stirred solution containing 31 mg (40 imol) of phosphate ester 70 in 0.45 mL of anh dichloromethane was added a solution of 8.0 mg (30 imol) of CBzprotected linker 44 in 0.45 mL of anh dichloromethane at 0 C. To the reaction mixture was added 12 tL (15 mg, 80 imol) of TMSOTf and the reaction mixture was stirred at 0 C for 15 mm. The reaction mixture was poured into a mixture of 10 mL of ethyl acetate and 10 mL satd aq NaHCO3. The aqueous and organic layers were separated and the organic layer was washed with three 1 0-mL portions of water and brine and then dried (MgSO4). The solvent was concentrated under diminished pressure to afford a crude residue. The residue was applied to a silica gel colunm (25 x 2 cm). Elution with 12:12:1 ethyl acetate-hexanes-methanol afforded 72 as a colorless oil: yield 15mg (48%); silica gel TLC Rf 0.17(11:11:1 ethyl acetate-hexanes-methanol); ?H NMR (CDC13) oe ?H NMR (CDC13) oe 1.95-2.07 (m, 6H), 2.07-2.15 (m, 12H), 3.41 (t, 2H, J= 9.5 Hz), 3.59 (d, 2H, J 5.0Hz), 3.61-3.71 (m, 3H), 3.87 (dt, 1H, J= 12.8 and 6.5 Hz), 3.94-4.04 (m, 1H),4.04-4.20 (m, 3H), 4.21-4.26 (m, 1H), 4.36-4.48 (m, 1H), 4.49-4.60 (m, 1H), 4.75(d, 1H, J= 7.5 Hz), 4.84-5.05 (m, 4H), 5.05-5.20 (m, 4H), 5.21-5.29 (m, 1H), 5.32-5.49 (m, 2H) and 7.27-7.3 8 (m, 5H) ; ?3C NMR (CDC13) oe 20.75, 20.77, 20.82,20.85, 20.88, 20.92, 40.9, 62.1, 62.3, 62.6, 65.1, 65.2, 66.9, 67.8, 68.1, 68.5, 68.6,69.2, 70.37, 70.45, 99.5, 128.3, 128.4, 128.5, 128.7, 136.6, 155.7, 169.0, 169.4,169.61, 169.65, 170.6, 170.82 and 170.89; HRMS (APCI), m/z 859.2973 (M + H)(C37H51N2021 requires m/z 859.2984).

Reference： [1]Patent: WO2014/145109,2014,A1 .Location in patent: Paragraph 0292
[2]Patent: WO2014/152718,2014,A1 .Location in patent: Paragraph 0284; 0291

40
1,3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-(methylcarbamoyl)-α-D-altropyranosyl)-β-L-gulopyranosyl diphenylphosphate [ No CAS ]
[ 145881-74-9 ]
3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-(methylcarbamoyl)-α-D-altropyranosyl)-α,β-L-gulopyranosyl benzyl 2-(2-ethoxy)ethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 15h;	[0296] 3, 6-Tri-O-a?tyi-2-0^2 ,6-tr^^ D-alfrop ranos l}-o4 -I -gl<>pv t anf.svl Benzyl 2-<2~Ethoxy)ethykarbainate (82), To a stirred solution containing 17 mg (19 prnol) of phosphate ester SO in 0.25 rnL of anh dichloromeihane was added a solution of 5.0 mg (17 mutauetaomicron) of ?Bz~protected linker 54 in 0.25 ml, of anh dichloromeihane at 0 'C. To the reaction mixture was added 7.0 pL (8.6 mg, 34 pmol) of TMSOTf The reaction mixture was stirred at 0 C for 15 rain and then poured into a .mixture of 10 rnL ethyl acetate and 10 mL satd aq NaHC<. The aqueous and organic layers were separated and the organic layer was washed with three 10-raL portions of distilled water and brine aid then dried (MgSOf). The solvent was concentrated under diminished pressure to afford a crude residue. The residue was applied to a silica gel column (25 x 2 cm). Elation with 12:1.2:1 ethyl actate--hexaaes--metaiTol afforded 82 as a colorless oil: yield 10 mg (59%); silica, gel TLC 0, 14 (I 1 : 11 : 1 ethyl acetate-hexanes-methaiiol); N R (CDCK) delta 1.97 id, 3H, J FontWeight="Bold" FontSize="10" 8,6 Hz), 2.04 (d, ,J FontWeight="Bold" FontSize="10" 4.2 Hz), 2.07-2.15 (m, 12H), 2,75 (d, 3H, J - 4.7 Hz), 3.34-3.44 (ra, 2H), 3.51-3.70 (ni 8H), 3.72 (dd5 HI J ::: 10.3 and 5.6 Hz), 3.82-3.93 (m, I H), 3.95- 4.25 (m, 3M), 4.26-4.56 (m, IH), 4.63 (d, IH, 7.2 Hz), 4.86-5.02 (rn, 1 H), 4.96- 5.28 (ra, 6H), 5.33-5.5 (m, IH), 5.83 (d, IH, J - 4.7 Hz) and 7.27-7.39 (ra, 5H); C NMR (CDCb) delta 20.79, 20.84, 20.86, 20.89. 20.93, 21.0, 29.8, 41.0, 61.9, 62.2, 62.3, 62,7, 62.9, 65.26, 65.33, 66.9, 67, 1, 70.2, 70.4, 70.5. 72,3, 128.3, 128.4, 128.66, 128.67, 136.6, 169.61 , 169.65, 169.68, 170.6, 170.7, .170.8 and 170.9; HRMS (APC m/z 8 ffi& 873.3141).

Reference： [1]Patent: WO2014/145109,2014,A1 .Location in patent: Paragraph 0296

41
[ 162111-85-5 ]
[ 145881-74-9 ]
2,4,6-tri-O-acetyl-3-O-(carbamoyl)-α-D-mannopyranosyl benzyl 2-(2-ethoxy)ethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.333333h;	0322) 2,4,6-tri- -aeeryi-3~0-(carbam Benzyl 2- (Erhoxy)ethylcarbamate (103). To a aoSoiion of 121 mg (0.21 ramoi) of 89 and 45 mg (0.19 niraol) of 54 in 3.5 rL of anhydrous CHjCh was added 68 pL (83 mg, 0.38 rarool) of TMSOTf at 0 C, The reaction mixture was stirred at 0 C for 20.rain, at which time it was poured into a two-phase solution, of EtOAc (70 mL) and saturated aq NaHCO* (28 mL), The organic layer was washed with two 28-mL portions of brine, dried (NasSO), filtered and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (25 2,5 era). Elution with 1: 1 1:2 -> 1 :3 hexanes-ethyl acetate afforded compound 103 as a colorless oil; yield 95 mg (80%); silica gei TLC - 0.26 (1 :3 hexanes-ethyl acetate); NMR (CDCU) delta 2.02 (s, 3H), 2.08 (s, 3H), 2.1.2 is, 3H), 3.39 (m, 2H), 3.54 (TO, 2H), 3.64 (m, 3H), 3.79 (m, 1 HQ, 4.08 (m, 2H)t 4.26 Cm, H), 4.71. (br s, 2H), 4.91 (s, IB), 5.10 (s, 2H), 5.25 (m, 3H), 5.37 (br s, 1H) and 7.35 (m, 5H); {3C NMR (CDC ) 8 20.8, 20.9, 21.0, 41.1 , 62.7, 66.5, 66.8, 67,3, 68,5, 70.0, 70.1, 70.3, 70.4, 77,4, 97.6, 128.1, 128,2, 128,6, .136.8, .155.3, 1.70.1, 170,2, 170.8.
80%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.333333h;	To a solution of 121 mg (0.21 mmol) of 82 and 45 mg (0.19 mmol) of 39 in 3.5 mL of anhydrous CH2C12 was added 68 tL (83 mg, 0.38 mmol) of TMSOTf at 0 C. The reaction mixture was stirred at 0 C for 20 mm, at which time it was poured into a two-phase solution of EtOAc (70 mL) and satd aq NaHCO3 (28 mL). The organic layer was washed with two 28-mL portions of brine, dried (Na2504), filtered and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (25 x 2.5 cm). Elution with 1:1 - 1 :2- 1:3 hexanes-ethyl acetate afforded compound 115 as a colorless oil: yield 95mg (80%); silica gel TLC Rf 0.26 (1:3 hexanes-ethyl acetate); ?H NMR (CDC13) oe 2.02 (s, 3H), 2.08 (s, 3H), 2.12 (s, 3H), 3.39 (m, 2H), 3.54 (m, 2H), 3.64 (m, 3H), 3.79 (m, 1H), 4.08 (m, 2H), 4.26 (m, 1H), 4.71 (br s, 2H), 4.91 (s, 1H), 5.10 (s, 2H), 5.25 (m, 3H), 5.37 (br s, 1H) and7.35 (m, 5H); ?3C NMR (CDC13) oe 20.8, 20.9, 21.0, 41.1, 62.7, 66.5, 66.8, 67.3,68.5, 70.0, 70.1, 70.3, 70.4, 77.4, 97.6, 128.1, 128.2, 128.6, 136.8, 155.3, 170.1,170.2, 170.8; mass spectrum (APCI), m/z 571.2141 (M + H) (C25H35N20,3 requires m/z 571.2139).

Reference： [1]Patent: WO2014/145109,2014,A1 .Location in patent: Paragraph 0322
[2]Patent: WO2014/152718,2014,A1 .Location in patent: Paragraph 0325; 0326

42
[ 162111-91-3 ]
[ 145881-74-9 ]
3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl benzyl 2-(2-ethoxy)ethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.283333h;	(03091 3 ,6-Tri- -acetyI-2- K2A6- i- -acet> -3- -cai t)antoyl-- - iTiaiinopYriinosyI)~-lj-giiJop raiH)sy benzyl 2~(2~ethoxy)eiiiyicar aoiaie (92). To a solution of 78 mg ( 1 muetaiotaomicron) of J and 19 mg (79 muetaiotaomicron) of 54 in 2.4 n L of anhydrous CH2C12 was added 28 uL (34 mg, 0.16 mmol) of TMSOTf at 0 aC. The reaction mixture was stirred at 0 C for 1.7 rain, at which time it was poured into a two-phase solution of EtOAc (50 ml,) and saturated aq NaHCOj (20 mL). The organic layer was washed, with two 20- L portions of brine, dried ( a^SC^), filtered and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (25 * 2 em). Elation with 15;32; 1 - 1.1 :36:1 hexanes-ethyl acetate- methanol afforded compound 92 as a colorless oil: yield 62 mg (80%); silica gei TLC /if 0.30 (1 :4 hexanes-etliyl acetate); NMR (CDCfe) delta 2.03 (s, 6E), 2.07 (s, 3H), 2.09 (s, 3H), 2.1 1 (s, 3H), 2.12 (s, 3H), 3.54 (m, 8H), 3,83 (m, I H), 3.96 (m, GammaEta), 4.05 (in, 4H), 4,25 (m, iH), 4.46 (ra, I B), 4.69 (s, I H), 4.91. (m, I H), 5.12 (m, 8H), 5.61 (ra, I H) and 7.34 (m, 5H); NMR (CDC1. S 20.6, 20.7, 20,8, 29.6, 40.9, 62.1, 62.5, 63,7, 65.5, 66 J , 66.6, 67.6, 68.5, 69.1 , 69,6, 69.7, 70.0, 70,3, 70.6, 97.0, 97.1, 128. 1, 128,2, 128.4, 136.5, 156.5, 169.3, 1 9,5, 1 9.8 and 170.5.

Reference： [1]Patent: WO2014/145109,2014,A1 .Location in patent: Paragraph 0309

43
[ 141607-25-2 ]
[ 145881-74-9 ]
[ 1433192-30-3 ]

Yield	Reaction Conditions	Operation in experiment
37%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.3h;	{OSSSJ 2 i4,6-Tetra- -acet> --0-mannt)pyrant)syl benxyl 2-(2- ctho:sy)eihjkarbainaie (til). To a solution of 300 mg (0.52 mmol) of phosphate ester 110 and 1 1 1 mg (0.46 mmol) of the alcohol 54 in 5.5 mL of anhydrous CHiC , was added 1 8 uL (207 mg, 0.93 mmol) of TMSOTf at 0 X,. The reaction was stirred at 0 aC for 18 mm and was then poured into a two-phase solution of EtOAc (1 0 ml) and saturated aq NaHCO } (40 mL). The organic layer was washed with two 40-raL portions of brine, dried { ajSQt), filtered and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica ge column (2.5x25 cm). ESotion with 2: l-> 1 :2 hexanes-ethyl acetate afforded compound ill as a colorless oil: yield 1 10 rag {37%); silica gel TLC l/ 0.35 (1 :3 hexanes-ethyl acetate); FontWeight="Bold" FontSize="10" H N R <CDC) delta l ,6I (s, 1 H), 1.96 (s, 311), 1.98 (, 3H), 2.06 (s, 3H), 2.11 (s, 311), 3.38 (m, 2H), 3.53 (m, 2.B.), 3.63 (m, 3H), 3.77 (m, TH), 4.05 (m, IB), 4.09 (m, 1H), 4.24 (dd, 1 H, J - 12.4 and 5.2 Hz), 4,87 (d, 1 H, J - 1.2 Hz), 5.08 (s, 2H), 5.22 (m, 1H), 5.26 (m, 1H), 5.31 (br s, 1 H), S.34 (m, 5H), 7.26-7.34 (m, 5H); C NMR (CDC) delta 20.80, 20.82, 20.9, 21.0, 39.4, 41.1, 62.7, 66.4, 66,8, 67.2, 68.6, 69. 1 , 69.8, 70.1 , 70.4, 97.7, 128.2, 128.6, 136.8, 169.9, 170.0, 170.3, 170.8 and 170.9; mass spectrum (MALDI), m/z 592.34 (M + af ; mass spectrum (APCI), m/z 570.21 2 (M + E)"" (Cjfii-lsft Oi , requires m/z 570.2187).
37%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.3h;	To a solution of 300 mg (0.52 mmol) of phosphate ester 120 and 111 mg (0.46 mmol) of the alcohol 39 in 5.5 mL of anhydrous CH2C12, was added 168 tL (207 mg, 0.93 mmol) of TMSOTf at 0 C. The reaction was stirred at 0 C for 18 mm and was then poured into a two-phase solution of EtOAc (100 mL) and satd aq NaHCO3 (40 mL). The organic layer was washed with two 40-mL portions of brine, dried (Na2SO4), filtered and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel colunm (2.5 x 25 cm). Elution with 2:1 - 1:2 hexanes-ethyl acetate afforded compound 121 as a colorless oil: yield 110 mg (37%); silica gel TLC Rf 0.35 (1:3 hexanes-ethyl acetate); ?HNMR (CDC13) oe 1.61(s, 1H), 1.96 (s, 3H), 1.98 (s, 3H), 2.06 (s, 3H), 2.11 (s, 3H), 3.38 (m, 2H), 3.53 (m, 2H), 3.63 (m, 3H), 3.77 (m, 1H),4.05 (m, 1H), 4.09 (m, 1H), 4.24 (dd, 1H, J 12.4 and 5.2 Hz), 4.87 (d, 1H, J= 1.2 Hz), 5.08 (s, 2H), 5.22 (m, 1H), 5.26 (m, 1H), 5.31 (br s, 1H), 5.34 (m, 5H), 7.26- 7.34 (m, 5H); ?3C NMR (CDC13) oe 20.80, 20.82, 20.9, 21.0, 39.4, 41.1, 62.7, 66.4,66.8, 67.2, 68.6, 69.1, 69.8, 70.1, 70.4, 97.7, 128.2, 128.6, 136.8, 169.9, 170.0,170.3, 170.8 and 170.9; mass spectrum (MALDI), m/z 592.34 (M + Na) mass spectrum (APCI), m/z 570.2182 (M + H) (C26H36N013 requires m/z 570.2187).

Reference： [1]Patent: WO2014/145109,2014,A1 .Location in patent: Paragraph 0333
[2]Patent: WO2014/152718,2014,A1 .Location in patent: Paragraph 0333

44
1,3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-(methylcarbamoyl)-α-D-altropyranosyl)-β-L-gulopyranosyl diphenylphosphate [ No CAS ]
[ 145881-74-9 ]
1,3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-(methylcarbamoyl)-α-D-altropyranosyl)-β-L-gulopyranosyl benzyl 2-(2-ethoxy)ethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	To a stirred solution containing 17 mg (19 imol) of phosphate ester 71 in 0.25 mL of anh dichloromethane was added a solution of 5.0 mg (17 imol) of CBz-protected linker 44 in 0.25 mL of anh dichloromethane at 0 C. To the reaction mixture was added 7.0 tL (8.6 mg, 34 imol) of TMSOTf. The reaction mixture was stirred at 0 C for 15 mm and then poured into a mixture of 10 mL ethyl acetate and 10 mL satd aq NaHCO3. The aqueous and organic layers were separated and the organic layer was washed with three 1 0-mL portions of distilled water and brine and then dried (MgSO4). The solvent was concentrated under diminished pressure to afford a crude residue. The residue was applied to a silica gel colunm (25 x 2 cm). Elution with 12:12:1 ethyl acetate-hexanes-methanol afforded 73 as a colorless oil: yield 10mg (59%); silica gel TLC Rf 0.14(11:11:1 ethyl acetate-hexanes-methanol); ?H NMR (CDC13) oe 1.97 (d, 3H, J = 8.6 Hz), 2.04 (d, 3H, J= 4.2 Hz), 2.07-2.15 (m, 12H), 2.75 (d, 3H, J= 4.7 Hz), 3.34-3.44 (m, 2H), 3.51-3.70 (m, 8H), 3.72 (dd, 1H, J= 10.3 and 5.6 Hz), 3.82-3.93 (m, 1H), 3.95-4.25 (m, 3H), 4.26-4.56 (m, 1H), 4.63 (d, 1H, J= 7.2 Hz), 4.86-5.02 (m, 1H),4.96-5.28 (m, 6H), 5.33-5.5 1 (m, 1H), 5.83 (d, 1H, J= 4.7 Hz) and 7.27-7.39 (m, 5H); ?3C NMR (CDC13) oe 20.79, 20.84, 20.86, 20.89, 20.93, 21.0, 29.8, 41.0, 61.9,62.2, 62.3, 62.7, 62.9, 65.26, 65.33, 66.9, 67.1, 70.2, 70.4, 70.5, 72.3, 128.3, 128.4,128.66, 128.67, 136.6, 169.61, 169.65, 169.68, 170.6, 170.7, 170.8 and 170.9; HRMS (APCI), m/z 873.3150 (M + H) (C38H53N202, requires m/z 873.3141).

Reference： [1]Patent: WO2014/152718,2014,A1 .Location in patent: Paragraph 0284; 0295

45
[ 162111-91-3 ]
[ 145881-74-9 ]
3,4,6-tetra-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl)-α-L-gulopyranosyl benzyl 2-(2-ethoxy)ethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.283333h;	To a solution of 78 mg (91 imol) of 84 and 19mg (79 imol) of 39 in 2.4 mL of anhydrous CH2C12 was added 28 tL (34 mg, 0.16 mmol) of TMSOTf at 0 C. The reaction mixture was stirred at 0 C for 17 mm, at which time it was poured into a two-phase solution of EtOAc (50 mL) and satd aq NaHCO3 (20 mL). The organic layer was washed with two 20-mL portions of brine, dried (Na2SO4), filtered and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (25 x 2 cm). Elution with 15:32:1 - 11:36:1 hexanes-ethyl acetate-methanol afforded compound 85 as a colorless oil:yield 62 mg (80%); silica gel TLC Rf 0.30 (1:4 hexanes-ethyl acetate); ?H NMR (CDC13) oe 2.03 (s, 6H), 2.07 (s, 3H), 2.09 (s, 3H), 2.11 (s, 3H), 2.12 (s, 3H), 3.54 (m, 8H), 3.83 (m, 1H), 3.96 (m, 1H), 4.05 (m, 4H), 4.25 (m, 1H), 4.46 (m, 1H), 4.69 (s, 1H), 4.91 (m, 1H), 5.12 (m, 8H), 5.61 (m, 1H) and 7.34 (m, 5H); ?3C NMR (CDC13) oe 20.6, 20.7, 20.8, 29.6, 40.9, 62.1, 62.5, 63.7, 65.5, 66.1, 66.6, 67.6, 68.5, 69.1, 69.6, 69.7, 70.0, 70.3, 70.6, 97.0, 97.1, 128.1, 128.2, 128.4, 136.5, 156.5,169.3, 169.5, 169.8 and 170.5.

Reference： [1]Patent: WO2014/152718,2014,A1 .Location in patent: Paragraph 0301; 0310

46
3,4,6-tetra-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-L-gulopyranosyl diphenylphosphate [ No CAS ]
[ 145881-74-9 ]
C₃₈H₅₁NO₂₁ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.283333h;	. To a solution of 26mg (30 imol) of phosphate ester 171 and 6.5mg (27imol) of the alcohol 39 in 1.0 mL of anhydrous CH2C12 was added 10 tL (12.3 mg; 54 imol) of TMSOTf at 0 C. The reaction was stirred at 0 C for 17 mm and was then poured into a two-phase solution of EtOAc (50 mL) and satd aq NaHCO3 (20 mL). The organic layer was washed with two 20-mL portions of brine, dried (Na2SO4), filtered and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (25 x 2 cm). Elution with 32:16:1 - 12:12:1 hexanes-ethyl acetate-methanol afforded compound 175 as a colorless oil: yield 18mg (70%); silica gel TLC Rf 0.80 (12:12:1 hexanes-ethyl acetate-methanol); ?H NMR (CDC13) oe 1.97 (s, 3H), 2.02 (s, 3H), 2.04 (s, 3H), 2.08 (s, 3H), 2.10 (s, 3H), 2.12 (s, 3H), 2.14 (s, 3H), 3.40 (m, 2H), 3.61 (m, 3H),3.68 (m, 2H), 3.85 (m, 1H), 3.97 (m, 1H), 4.18 (m, 5H), 4.27 (m, 4H), 4.47 (t, 1H, J= 6.4 and 6.4 Hz), 4.92 (d, 1H, J= 3.7 Hz), 5.01 (m, 2H), 5.09 (s, 2H), 5.15 (s, 1H), 5.28 (m, 3H), 5.45 (s, 1H) and 7.33 (m, 5H); ?3C NMR (CDC13) oe 20.61,20.62, 20.70, 20.75, 20.8, 29.7, 40.9, 62.1, 62.5, 63.7, 65.5, 6.0, 66.6, 68.6, 68.6,69.1, 69.2, 70.1, 70.3, 70.6, 97.0, 97.1, 128.05, 128.15, 128.5, 136.5, 156.4, 169.3,169.5, 169.6, 169.8, 169.9, 170.52 and 170.53; mass spectrum (ESI), m/z 858.3036 (M + H) (C38H52N02, requires m/z 858.3026).

Reference： [1]Patent: WO2014/152718,2014,A1 .Location in patent: Paragraph 0319; 0320

47
3,4,6-tetra-O-acetyl-2-O-(2,3,6-tri-O-acetyl-4-O-(methylcarbamoyl)-α-D-mannopyranosyl)-β-L-gulopyranosyl diphenylphosphate [ No CAS ]
[ 145881-74-9 ]
3,4,6-tetra-O-acetyl-2-O-(2,3,6-tri-O-acetyl-4-O-(methylcarbamoyl)-α-D-mannopyranosyl)-β-L-gulopyranosyl benzyl 2-(2-ethoxy)ethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0℃; for 0.25h;	To a stirred solution containing 38.0 mg (0.04 mmol) of phosphate ester 60 in 0.5 mL of anh dichioromethane was added a solution of 10.0 mg (0.04 mmol) of CBz-protected linker 39 in 0.5 mL of anh dichloromethane at 0 C. To the cooled reaction mixture was then added 14.0 tL (17.0 mg, 0.08 mmol) of TMSOTf. The reaction mixture was stirred at 0 C for 15 mm and then poured into a mixture of 20 mL of ethyl acetate and 20 mL of satd aq NaHCO3. The aqueous and organic layers were separated and the organic layer was washed with three 1 0-mL portions of water and brine and then dried (MgSO4). The solvent was concentrated under diminished pressure to afford a crude residue. The residue was applied to a silica gel colunm (25 x 3 cm). Elution with 12:12:1 ethyl acetate-hexanes-methanol afforded 61 as a colorless oil. The product isolated as a mixture of anomers: yield 19 mg (51%); silica gel TLC Rf 0.14 (12:12:1 ethyl acetate-hexanes-methanol); ?H NMR (CDC13) oe 1.92-2.14 (m, 18H), 2.71 (t, 3H, J 4.1 Hz), 3.40 (d, 3H, J= 4.9 Hz), 3.52-3.77 (m, 8H), 3.85 (dd,1H, J= 8.4 and 3.2 Hz), 3.95 (t, 1H, J 3.9 Hz), 4.27 (dd, 2H, J= 13.4 and 7.3 Hz), 4.40 (t, 1H, J= 6.4 Hz), 4.88-5.04 (m, 3H),5.05-5.22 (m, 6H), 5.25 (dd, 1H, J 7.3 and 3.6 Hz) and 7.28-7.40 (m, 5H); ?3C NMR (CDC13) oe 20.78, 20.83 20.85, 20.87, 20.92, 20.95, 27.7, 61.9, 62.3, 63.1, 63.8, 65.7, 66.8, 66.9, 68.1, 68.7, 68.8, 69.6, 69.8, 70.2, 71.0, 72.3, 97.2, 97.5,128.27, 128.33, 128.65, 128.67, 169.5, 169.7, 169.8, 169.9, 170.57, 170.63 and170.7; HRMS (APCI), m/z 873.3142 (M + H) (C38H53N202, requires m/z873.3141).

Reference： [1]Patent: WO2014/152718,2014,A1 .Location in patent: Paragraph 0267; 0278

48
[ 5292-43-3 ]
[ 145881-74-9 ]
N-(benzyloxycarbonyl)-2-(2-(2-aminoethoxy)ethoxy)acetate tert-butyl ester [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 10310 - 10323
[2]Chemical Communications,2019,vol. 55,p. 1821 - 1824

49
[ 76101-29-6 ]
[ 145881-74-9 ]
benzyl 4-(benzyloxy)-3-isopropyl-2-methyl-5,8-dioxa-3-aza-4-phosphadecan-10-ylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		A solution of 1H-tetrazole (~0.45 M in acetonitrile, 2.5 mL, 1.15 mmol) was added tobenzoyloxydichlorophosphine (1.0 M in dichloromethane; 1.5 mL, 1.5 mmol) andstirred for 1 hour at room temperature. To this was added a solution of the alcohol 11(100 mg, 0.42 mmol) in dichloromethane (1.5 mL) and stirring continued for a further18 hours. The mixture was diluted with water (10 mL) and extracted withdichloromethane (3 x 20 mL). The combined organic layers were washed withsaturated aqueous sodium hydrogen carbonate and brine, then dried (MgSO4), filteredand concentrated to dryness. Purification by flash chromatography (50% ethyl acetatein petroleum spirits) gave the product 12 (160 mg, 82%) as a pale yellow oil. Theproduct was then dissolved in 2 mL of dichloromethane and stored at 4 C. Rf 0.90 (50% ethyl acetate in petroleum spirits); H (500 MHz; CDCl3) 7.36-7.24(10H, m), 5.30 (1H, br s), 5.08 (2H, s), 4.77-4.60 (2H, m), 3.85-3.68 (2H, m), 3.64-3.60 (4H, m), 3.56-3.54 (2H, m), 3.38-3.35 (2H, m), 1.17 (12H, d, J = 6.5 Hz); P (202MHz; CDCl3) 147.75. C (125 MHz; CDCl3) 156.4, 139.4, 136.6, 128.4, 128.2, 128.1 128.0, 127.2, 127.012, 71.2, 71.1, 69.9, 66.6, 65.4, 65.2, 62.8, 62.6, 43.0, 42.9, 40.9,24.6, 24.5; P (202 MHz; CDCl3) 147.7; HRMS (ESI+) 477.2539 (477.2518 calculatedfor C25H38N2O5P (M+H)+).

Reference： [1]Synlett,2016,vol. 27,p. 121 - 125

50
[ 124-63-0 ]
[ 145881-74-9 ]
[ 281206-42-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine; In dichloromethane; at 0 - 20℃; for 1h;	To a solution of <strong>[145881-74-9]benzyl N-[2-(2-hydroxyethoxy)ethyl]carbamate</strong> (1 g, 4.18 mmol) and TEA (1.27 g, 12.5 mmol, 1.75 mL) in DCM (10 mL) was added MsCl (574 mg, 5.02 mmol, 388 uL) at 0 C. The reaction mixture was stirred at 20 C. for 1 hour. On completion, the mixture was quenched with the addition of H2O (30 mL), then exacted with DCM (2×50 mL). The organic phase was concentrated in vacuo to give a title compound (1.30 g, 98% yield) as yellow oil. LC-MS (ESI+) m/z 318.2 (M+H)+.
24 g	In dichloromethane; at 20℃;Inert atmosphere;	CBZ-Methanesulfonyl chloride (7.1 ml) dissolved in anhydrous dichloromethane (70 ml) was slowly added to the product (9) of step A, and the mixture was stirred overnight at room temperature under nitrogen atmosphere. The mixture was filtered, stirred 1 h with solid Na2CO3 (26.6 g), and refiltered. The filtrate was concentrated under reduced pressure, the residue was re-dissolved in toluene (150 ml), and the resulting solution was filtered and concentrated by distillation under reduced pressure. The residue was dried overnight under vacuum, giving 24 g of the desired product (10).

Reference： [1]MedChemComm,2019,vol. 10,p. 1037 - 1041
[2]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 2956; 2958
[3]Patent: US9173951,2015,B2 .Location in patent: Page/Page column 125

51
[ 13139-17-8 ]
[ 929-06-6 ]
[ 145881-74-9 ]

Yield	Reaction Conditions	Operation in experiment
40 g	With triethylamine; In dichloromethane; at 20℃;	To 2-(2-aminoethoxyl)ethanol (20 g) dissolved in dichloromethane (200 ml) was added stepwise triethylamine (26.5 ml) and benzyloxy(carbonyloxy)succinimide (47.47 g). The reaction mixture was stirred overnight at room temperature. The solvent was distilled off under reduced pressure and the residue was dissolved in deionized water (500 ml). The insoluble layer was separated, and the aqueous layer was mixed with 50 g of NaCl and the pH adjusted to 5.0 with 5% H3PO4. The product was extracted with dichloromethane (100 ml, 50 ml, and 50 ml) and the extract was dried with MgSO4, filtered, and evaporated to dryness under reduced pressure. The residue was dried under vacuum overnight, then combined with the previously separated insoluble layer and dissolved in dichloromethane (300 ml). The solution was washed with 5-% aqueous NaCl solution (3×50 ml) and dried with MgSO4. The solvent was distilled under reduced pressure, and the residue was dried overnight under vacuum, giving 40 g of the desired product.

Reference： [1]Patent: US9173951,2015,B2 .Location in patent: Page/Page column 125

52
[ 145881-74-9 ]
2-(N-benzyloxycarbonyl-2-aminoethoxy)-1-bromoethane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃; for 1.5h;	General procedure: The above protected aminoalcohol (2 mmol) was dissolved in CH2Cl2 (15 mL) and CBr4 (0.990 g, 2.98 mmol) and Ph3P (0.783 g, 2.98 mmol) were added to the stirred solution at 0 C. The solution was warmed at room temperature and the reaction was followed by TLC (Petroleum ether/EtOAc 7/3). After 90 min at r.t. water was added in the reaction flask. The solution was diluted with CH2Cl2 (110 mL) and the organic phase was washed twice with water and brine, dried over Na2SO4 and the solvent evaporated to dryness under vacuum. The crude material was purified by flash chromatography (SiO2, petroleum ether/AcOEt 90/10, gradient 2%) to give the bromide as a transparent oil. 4.1.3 2-(N-Benzyloxycarbonyl-2-aminoethoxy)-1-bromo-ethane (19) Yield 77%; Rf = 0.4 (petroleum ether/AcOEt 6:4); 1H NMR, (CDCl3) delta: 3.41 (q, 2H, J = 5.2 Hz); 3.45 (t, 2H, J = 6.0 Hz); 3.57 (t, 2H, J = 5.2 Hz); 3.76 (t, 2H, J = 6.0 Hz); 5.11 (s, 2H); 7.32-7.36 (m, 5H); 13C NMR, (CDCl3) delta: 30.3 (t); 40.7 (t); 66.5 (t); 69.7 (t); 70.6 (t); 127.9 (d); 128.2 (d); 136.4 (s); 156.3 (s). ESI-MS (m/z): 304.0 [M + H+]; 324.1 [M + Na+]; 340.0 [M + K+]; 318.9 [M + NH4+].

Reference： [1]Tetrahedron,2017,vol. 73,p. 3014 - 3024

53
[ 145881-74-9 ]
all-cis-3,5-N,N-di-tert-butyloxycarbonyl-1-N-[2-(N-benzyloxycarbonyl-2-aminoethoxy)ethyl]-1,3,5-triaminocyclohexane [ No CAS ]

Reference： [1]Tetrahedron,2017,vol. 73,p. 3014 - 3024

54
[ 145881-74-9 ]
all-cis-5-N-tert-butyloxycarbonyl-1,3-N,N-di-[2-(N-benzyloxycarbonyl-2-aminoethoxy)ethyl]-1,3,5-triaminocyclohexane [ No CAS ]

Reference： [1]Tetrahedron,2017,vol. 73,p. 3014 - 3024

55
[ 145881-74-9 ]
benzyl (2-(2-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethyl)carbamate [ No CAS ]

Reference： [1]Patent: WO2018/6063,2018,A1

56
[ 106929-82-2 ]
[ 145881-74-9 ]
benzyl (2-{2-[(2,3,4-tri-O-acetyl-6-deoxy-alpha-L-mannopyranosyl)thio]ethoxy}ethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,1'-azodicarbonyl-dipiperidine; trimethylphosphane; In tetrahydrofuran; at 0 - 20℃; for 2h;	Trimethylphosphine (TMP, 1 .0M in THF, 1 .3 mL, 1 .3 mmol) was added to a solution of 1 ,1 '- (azodicarbonyl)dipiperidine (ADDP, 0.329 g, 1 .3 mmol) in 2 mL of THF at 0 C and stirred for 30 min. The Cbz-2-(2-hydroxyethoxy)ethyl alcohol (0.164 g, 0.686 mmol) from Step a and the 2,3,4-tri-0-acetyl-6- deoxy-1 -thio-alpha-L-mannopyranose from Step b (in 2 mL of THF) were added sequentially to the solution, with further stirring at room temperature for 2 hours. Any precipitate was then filtered off and the solution evaporated to dryness. Normal phase silica gel column purification (0-70% EtOAc/Hex) gave the desired product as a white foam (0.946 g, 80%). 1 H NMR (300 MHz, Chloroform-d): delta 7.42 - 7.28 (m, 5H), 5.40 - 5.25 (m, 2H, NH, CH), 5.28 (d, J = 1 .5 Hz, 1 H), 5.22 (dd, J = 10.0, 3.3 Hz, 1 H), 5.17 - 5.05 (m, 3H), 4.20 (m, 1 H), 3.64 (m, 2H), 3.53 (m, 2H), 3.38 (m, 2H), 2.84 (m, 1 H), 2.72 (m, 1 H), 2.13 (s, 3H), 2.05 (s, 3H), 1 .99 (s, 3H), 1 .23 (d, J = 6.2 Hz, 3H). 13C NMR (75 MHz, CDCI3) delta 170.19 (e), 169.99 (e), 169.88 (e), 156.47 (e), 136.57 (e), 128.50 (o, 2C), 128.07 (o, 3C), 82.64 (o), 77.52 (CDCI3), 77.09 (CDCI3), 76.67 (CDCI3), 71 .52 (o), 71 .1 5 (o), 70.55 (e), 69.94 (e), 69.24 (o), 67.1 9 (o), 66.64 (e), 40.87 (e), 30.72 (e), 20.95 (o), 20.82 (o), 20.70 (o), 1 7.37 (o).

Reference： [1]Patent: WO2018/6063,2018,A1 .Location in patent: Page/Page column 189; 190

57
[ 145881-74-9 ]
[ 30021-94-4 ]
(2R,3R,4R,5S,6S)-2-(2-(2-(((benzyloxy)carbonyl)amino)ethoxy)ethoxy)-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With boron trifluoride diethyl etherate; In dichloromethane;Cooling with ice;	To a solution of benzyl (2-(2-hydroxyethoxy)ethyl)carbamate (14g, 56 mmol) and per-acetyl-L- rhamnose (20 g, 56 mmol) in 200 mL dry DCM under the ice-water bath, then BF3-Et20 (15 mL, 1 10 mmol) was added dropwise to the above cooled solution. After stirring overnight, the reaction was quenched with saturated NaHCCb (aq) and diluted with EtOAc. The organic phase was washed sat. NaHC03 (aq) and brine. The combined organic layers were dried over anhydrous Na2S04. The resultant solution was concentrated and purified by reversed phase liquid chromatography (RPLC) using an Isco CombiFlash liquid chromatograph eluted with 5% to 1 00% acetonitrile and water, using 0.1 % trifluoroacetic acid as the modifier. The product was isolated as an oil, 18 g (63%). LC/MS [M]+1 512.2.

Reference： [1]Biomacromolecules,2020,vol. 21,p. 793 - 802
[2]Patent: WO2018/6063,2018,A1 .Location in patent: Page/Page column 175-176

58
[ 145881-74-9 ]
[ 1290627-95-0 ]

Reference： [1]Patent: WO2018/129552,2018,A1
[2]MedChemComm,2019,vol. 10,p. 1037 - 1041

59
[ 145881-74-9 ]
tert-butyl N-[(1S)-1-[[2-(2-[[(benzyloxy)carbonyl]amino]ethoxy)ethyl]carbamoyl]-3-(methylsulfanyl)propyl]carbamate [ No CAS ]

Reference： [1]Patent: WO2018/129552,2018,A1

60
[ 145881-74-9 ]
tert-butyl N-[(1S)-1-[[2-(2-[[(benzyloxy)carbonyl]amino]ethoxy)ethyl]carbamoyl]-3-(dimethylsulfaniumyl)propyl]carbamate iodide [ No CAS ]

Reference： [1]Patent: WO2018/129552,2018,A1

61
[ 145881-74-9 ]
benzyl N-(2-[2-[(3S)-3-[[(tert-butoxy)carbonyl]amino]-2-oxopyrrolidin-1-yl]ethoxy]ethyl)carbamate [ No CAS ]

Reference： [1]Patent: WO2018/129552,2018,A1

62
[ 145881-74-9 ]
benzyl N-(2-[2-[(3S)-3-amino-2-oxopyrrolidin-1-yl]ethoxy]ethyl)carbamate [ No CAS ]

Reference： [1]Patent: WO2018/129552,2018,A1

63
[ 145881-74-9 ]
benzyl N-(2-(2-((3S)-3-((4-(benzyloxy)-3-methylbenzene)sulfonamido)-2-oxopyrrolidin-1-yl)ethoxy)ethyl)carbamate [ No CAS ]

Reference： [1]Patent: WO2018/129552,2018,A1

64
[ 136918-14-4 ]
[ 145881-74-9 ]
benzyl N-(2-(2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)ethoxy)ethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 40℃; for 1.5h;Inert atmosphere;	To a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was added alcohol INT-PI (5 g, 20.90 mmol, 1 equiv), phthalimide (3.07 g, 20.9 mmol, 1 equiv), and tetrahydrofuran (49 mL). This was followed by the addition of PPI13 (8.22 g, 31.34 mmol, 1.5 equiv) in several portions at 40 C. To tiiis was added DIAD (6.17 mL, 1.5 equiv) dropwise with stirring at 40 C over 30 min. The resulting solution was stirred for 1 h at 40 C in an oil bath. The resulting slurry was diluted with water and extracted with 3 x 100 mL of ethyl acetate. The organic layers combined and concentrated under vacuum The residue was applied onto a silica gel column with petroleum ether/ethyl acetate (1:1) providing 6.5 g (84%) of benzyl JV-[2-[2-(l,3-dioxo-2,3- dmydro-lH-isoindol-2-yl)ethoxy] ethyl] carbamate (INT-P2) as a yellow oil.

Reference： [1]Patent: WO2018/129552,2018,A1 .Location in patent: Paragraph 0425

65
3,4,6-tri-O-acetyl-2-O-(2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-manno-pyranosyl)-α-L-gulopyranosyl diphenylphosphate [ No CAS ]
[ 145881-74-9 ]
[ 1266609-55-5 ]

Reference： [1]New Journal of Chemistry,2019,vol. 43,p. 6010 - 6020

66
[ 145881-74-9 ]
[ 205535-92-8 ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 1821 - 1824

67
[ 145881-74-9 ]
[ 462100-03-4 ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 1821 - 1824

68
[ 105-36-2 ]
[ 145881-74-9 ]
ethyl 2-[2-[2-(benzyloxycarbonylamino)ethoxy]ethoxy]acetate [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 1821 - 1824

69
[ 145881-74-9 ]
benzyl (2-(2-azidoethoxy)ethyl)carbamate [ No CAS ]

Reference： [1]MedChemComm,2019,vol. 10,p. 1037 - 1041

70
[ 145881-74-9 ]
C₂₅H₂₆N₄O₇ [ No CAS ]

Reference： [1]MedChemComm,2019,vol. 10,p. 1037 - 1041

71
[ 145881-74-9 ]
tert-butyl 4-(2-(2-(((benzyloxy)carbonyl)amino)ethoxy)ethyl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/192668,2019,A1

72
[ 145881-74-9 ]
benzyl N-[2-(2-piperazin-1-ylethoxy)ethyl]carbamate hydrochloride [ No CAS ]

Reference： [1]Patent: US2019/192668,2019,A1

73
[ 145881-74-9 ]
tert-butyl N-[2-[2-[4-[2-[2-(benzyloxycarbonylamino)ethoxy]ethyl]piperazin-1-yl]ethoxy]ethyl]carbamate [ No CAS ]

Reference： [1]Patent: US2019/192668,2019,A1

Yield	Reaction Conditions	Operation in experiment
87.5%	With triethylamine; In tetrahydrofuran; at 20℃; for 1h;	General procedure: Glycolamine c (9.61 mmol) with different polymerization degrees was dissolved in 60 ml of tetrahydrofuran. At room temperature, triethylamine (9.62 mmol) and phenyl p-nitrochloroformate (10.62 mmol) were added separately. The mixture was further reacted at room temperature for 1 hour. TLC spot detection until the reaction is complete. Poured into 100 mL of ethyl acetate and 20 mL of water, extracted the organic layer, washed with saturated brine, concentrated and dried, and column chromatography (ethyl acetate: petroleum ether V: V = 1: 1), and finally obtained a white crystalline compound d1 (n = 0) or colorless oily compound d2 (n = 1).

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 145881-74-9 ]

Aryls

[ 165454-06-8 ]

3-Oxo-1-phenyl-2,7,10-trioxa-4-azadodecan-12-oic acid

Similarity: 0.91

[ 71811-26-2 ]

Benzyl (1,3-dihydroxypropan-2-yl)carbamate

Similarity: 0.89

[ 25070-73-9 ]

Benzyl morpholine-4-carboxylate

Similarity: 0.88

[ 72080-83-2 ]

Benzyl (2-aminoethyl)carbamate

Similarity: 0.87

[ 18807-71-1 ]

Benzyl N-(2-aminoethyl)carbamate hydrochloride

Similarity: 0.85

Ethers

[ 165454-06-8 ]

3-Oxo-1-phenyl-2,7,10-trioxa-4-azadodecan-12-oic acid

Similarity: 0.91

[ 139338-72-0 ]

1-(9H-Fluoren-9-yl)-3-oxo-2,7,10,13-tetraoxa-4-azapentadecan-15-oic acid

Similarity: 0.75

[ 260367-12-2 ]

2-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethoxy)acetic acid

Similarity: 0.75

[ 882847-32-7 ]

1-(9H-Fluoren-9-yl)-3-oxo-2,7,10,13,16,19-hexaoxa-4-azadocosan-22-oic acid

Similarity: 0.73

[ 867062-95-1 ]

1-(9H-Fluoren-9-yl)-3-oxo-2,7,10,13-tetraoxa-4-azahexadecan-16-oic acid

Similarity: 0.73

Alcohols

[ 71811-26-2 ]

Benzyl (1,3-dihydroxypropan-2-yl)carbamate

Similarity: 0.89

[ 17996-12-2 ]

Benzyl (6-hydroxyhexyl)carbamate

Similarity: 0.82

[ 87905-98-4 ]

Benzyl (5-hydroxypentyl)carbamate

Similarity: 0.82

[ 478646-28-5 ]

(R)-Benzyl (1,5-dihydroxypentan-2-yl)carbamate

Similarity: 0.81

[ 128117-22-6 ]

1-Cbz-3-Hydroxyazetidine

Similarity: 0.80

Amides

[ 165454-06-8 ]

3-Oxo-1-phenyl-2,7,10-trioxa-4-azadodecan-12-oic acid

Similarity: 0.91

[ 71811-26-2 ]

Benzyl (1,3-dihydroxypropan-2-yl)carbamate

Similarity: 0.89

[ 25070-73-9 ]

Benzyl morpholine-4-carboxylate

Similarity: 0.88

[ 72080-83-2 ]

Benzyl (2-aminoethyl)carbamate

Similarity: 0.87

[ 18807-71-1 ]

Benzyl N-(2-aminoethyl)carbamate hydrochloride

Similarity: 0.85

Amines

[ 165454-06-8 ]

3-Oxo-1-phenyl-2,7,10-trioxa-4-azadodecan-12-oic acid

Similarity: 0.91

[ 71811-26-2 ]

Benzyl (1,3-dihydroxypropan-2-yl)carbamate

Similarity: 0.89

[ 72080-83-2 ]

Benzyl (2-aminoethyl)carbamate

Similarity: 0.87

[ 18807-71-1 ]

Benzyl N-(2-aminoethyl)carbamate hydrochloride

Similarity: 0.85

[ 46460-73-5 ]

Benzyl (3-aminopropyl)carbamate

Similarity: 0.85

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 145881-74-9 ] {[proInfo.proName]}

Quality Control of [ 145881-74-9 ]

Related Doc. of [ 145881-74-9 ]

Product Details of [ 145881-74-9 ]

Calculated chemistry of [ 145881-74-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 145881-74-9 ]

Application In Synthesis of [ 145881-74-9 ]

[ 145881-74-9 ] Synthesis Path-Upstream 1~3

[ 145881-74-9 ] Synthesis Path-Downstream 1~74

Related Functional Groups of [ 145881-74-9 ]

Aryls

Ethers

Alcohols

Amides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 145881-74-9 ]