[ CAS No. 155130-15-7 ] {[proInfo.proName]}

Name: 155130-15-7|14-Hydroxy-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate|98%
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SKU: A1263601
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Quality Control of [ 155130-15-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 155130-15-7 ]

SDS Specification

Alternatived Products of [ 155130-15-7 ]

Product Details of [ 155130-15-7 ]

CAS No. :	155130-15-7	MDL No. :	MFCD22574780
Formula :	C₁₇H₂₈O₈S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NSODVVYOWINKAG-UHFFFAOYSA-N
M.W :	392.46	Pubchem ID :	15198040
Synonyms :		Chemical Name :	14-Hydroxy-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate

Calculated chemistry of [ 155130-15-7 ]

Physicochemical Properties

Num. heavy atoms :	26
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.65
Num. rotatable bonds :	16
Num. H-bond acceptors :	8.0
Num. H-bond donors :	1.0
Molar Refractivity :	94.35
TPSA :	108.9 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) :	-8.57 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.98
Log Po/w (XLOGP3) :	0.17
Log Po/w (WLOGP) :	1.84
Log Po/w (MLOGP) :	0.18
Log Po/w (SILICOS-IT) :	2.29
Consensus Log Po/w :	1.69

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.5
Solubility :	12.6 mg/ml ; 0.032 mol/l
Class :	Very soluble
Log S (Ali) :	-2.01
Solubility :	3.8 mg/ml ; 0.00967 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.81
Solubility :	0.00602 mg/ml ; 0.0000153 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.66

Safety of [ 155130-15-7 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 155130-15-7 ]

* 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 [ 155130-15-7 ]
Downstream synthetic route of [ 155130-15-7 ]

[ 155130-15-7 ] Synthesis Path-Upstream 1~1

1
[ 4792-15-8 ]
[ 98-59-9 ]
[ 41024-91-3 ]
[ 155130-15-7 ]

Reference： [1] Organic Letters, 2002, vol. 4, # 14, p. 2329 - 2332

[ 155130-15-7 ] Synthesis Path-Downstream 1~88

1
[ 155130-07-7 ]
[ 155130-15-7 ]
[ 155130-12-4 ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 3255 - 3278
[2]Angewandte Chemie,1993,vol. 105,p. 1791 - 1795

2
[ 100-02-7 ]
[ 155130-15-7 ]
2-[2-(2-{2-[2-(4-Nitro-phenoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethanol [ No CAS ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 2827 - 2830

3
[ 4792-15-8 ]
[ 98-59-9 ]
[ 155130-15-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	With sodium iodide; silver(I) oxide; In dichloromethane; at 0 - 20℃; for 1h;	To a solution of 3,6,9,12-tetraoxatetradecane-1,14-diol (10 g, 41.96 mmol, CAS4792-15-8), silver oxide (14.6 g, 62.94 mmol) and NaI (7 g, 46.56 mmol) in DCM (250 mL) was added tosyl chloride (8.5 g, 41.96 mmol) at 0 C. The reaction mixture was then allowed to warm to rt and stirred for 1 h. The reaction mixture was then filtered through celite and the filtrate was washed with 10% NaHCO3 solution (125 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was then evaporated under reduced pressure and the crude product was purified using silica gel column chromatography (3% MeOH-DCM) to give 14-hydroxy-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate as a yellow oil (13 g, 79%). LC-MS (ESI+) m/z 394.3 (M+H)+.
77%	With potassium iodide; silver(I) oxide; In dichloromethane;Cooling;	To a cold and stirred solution of pentaethylene glycol (1 eq) in DCM (amount×10 mL) were added Ag2O (1.5 eq), TsCl (1.1eq) and KI (0.2 eq). After stirring for 30 to 60 min, the precipitated silver salts were removed by filtration through a pad of Celite and washed thoroughly with EtOAc. The combined filtrate was concentrated under vacuum, and the residue was purified by silica gel chromatography to give a colorless oil, yield 77%. LC/MS (ESI) m/z: 393.2 [M+1] +; 1H-NMR (400MHz, CDCl3) d 2.45 (s, 3H), 3.59-3.73 (m, 18H), 4.16 (t, J = 4.8 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 7.80 (d, J = 8.0 Hz, 2H).
75%	With potassium iodide; silver(I) oxide; In dichloromethane; at 0℃; for 0.333333h;	14-Hydroxy-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate (26) To a chilled (0 C.) solution of pentaethylene glycol (2.13 g, 8.92 mmol) in DCM (89 mL) were added TsCl (1.87 g, 9.81 mmol), Ag2O (3.10 g, 0.134 mmol), and KI (0.296 g, 1.78 mmol). After stirring for 20 min the reaction mixture was filtered through a 4 cm pad of celite and flushed with EtOAc. The resulted filtrate was concentrated under reduced pressure to give a yellow oil. The crude product was purified via silica flash chromatography using 3:2 DCM/acetone as an eluent, providing 26 (2.63 g, 75%): 1H NMR (300 MHz, CDCl3) δ 7.80 (d, J=8.2 Hz, 2H), 7.34 (d, J=8.2 Hz, 2H), 4.20-4.11 (m, 2H), 3.76-3.54 (m, 18H), 2.44 (s, 3H).

74%	With triethylamine; In dichloromethane; at 0 - 20℃; for 18h;Inert atmosphere;	Protocole 2 A solution of pentaethylene glycol (0.04 mmol ; 25.00 g) in dry CH2Cl2 (15 mL), under argon, was cooled to 0C with an ice bath and triethylamine (0.015 mmol ; 2.10 mL). Subsequently p-toluenesulfonyl chloride (0.0104 mmol ; 1.98 g) was added in the portions to the cooled reaction mixture. After complete addition, the solution was allowed to warm to room temperature and was stirred for 18 h. The mixture was washed with water (3 x 100 mL), the aqueous layers were re-extracted with CH2Cl2 and the combined organic layers washed with 5% citric acid (3 x 25 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The product was purified by flash column chromatography on silica gel (99% CH2Cl2/MeOH) to give the desired compound 3e as a colorless oil in 74% yield (3.01 g).
69%		To a solution of 2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethanol (15 g, 62.95 mmol, 13.27 mL, 2 eq) in tetrahydrofuran (150 mL) was added sodium hydride (1.26 g, 31.48 mmol, 60% purity, 1 eq) at 0 C. The mixture was stirred at 0 C for 0.5 hour. Then p- toluenesulfonyl chloride (6.00 g, 31.48 mmol, 1 eq) was added, the mixture was stirred at 25 C for 2 hours. The mixture was poured into saturated ammonium chloride aqueous solution (100 mL), the water layer was extracted with ethyl acetate (80 mL x 2). Then the organic phase was dried over anhydrous sodium sulfate, filtered and the filtrate was condensed to get the residue. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 3/1 to dichloromathane/methanol = 10/1) to get 2-[2-[2-[2-(2- hydroxyethoxy)ethoxy] ethoxy] ethoxy] ethyl 4-methylbenzenesulfonate (8.62 g, 21.96 mmol, 69% yield) as a light yellow oil.
66%	With triethylamine; In dichloromethane; at 20℃; for 15h;	The compound tetrapentaethylene glycol (6.0 g, 25.2 mmol) was dissolved in 20 mL of dichloromethane, and triethylamine (4.9 g, 48, 4 mmol) was added dropwise while TsCl was placed in dichloromethane. The funnel was slowly added dropwise to the solution and stirred at room temperature for 15 h.The reaction was monitored by thin layer chromatography (EA) and the TsCl portion of the compound remained.The solution was adjusted to pH = 7 with 4M HCl, 10 mL of water was added, and extracted three times with 30 mL of dichloromethane.Column chromatography (EA) gave a product of 6.52 g, yield 66%.
61.22%	With silver(I) oxide; In dichloromethane; at 0 - 20℃; for 2h;	Into a 500-mL round-bottom flask, was placed 3,6,9,12-tetraoxatetradecane-1,14-diol (9.53 g, 39.995 mmol, 1 equiv) in dichloromethane (200 mL), to which was added Ag2O (13.90 g, 59.982 mmol, 1.50 equiv) and TsCl (7.78 g, 40.808 mmol, 1.02 equiv) at 0 in a water/ice bath. Then KI (1.33 g, 8.012 mmol, 0.20 equiv) was added. The resulting mixture was stirred for 2 hr at room temperature. The solids were filtered out and the filtrate was concentrated under vacuum. The residue was applied onto a silica gel column eluting with dichloromethane/methanol (12/1). This resulted in 9.61 g (61.22%) of 14-[(4- methylbenzenesulfonyl)oxy]-3,6,9,12-tetraoxatetradecan-1-ol as a light yellow oil. MS (ES+): m/z 392.95[MH+]
51%	With potassium iodide; In dichloromethane; at 20℃;	Into a 250-mL round-bottom flask, was placed a solution of 3,6,9,12-tetraoxatetradecan-1,14-diol (5.0 g, 20.98 mmol, 1.00 equiv) in dichloromethane (100 mL), Ag2O (7.3 g, 31.50 mmol, 1.50 equiv), 4-methylbenzene-1-sulfonyl chloride (4.0 g, 20.99 mmol, 1.00 equiv ), KI (695.0 mg, 4.19 mmol, 0.30 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of water (80 mL). The solids were filtered out. The resulting solution was extracted with dichloromethane (60 ml x 3) and the organic layers combined. The resulting mixture was washed with brine (60 ml x 1), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1/1). This resulted in 4.2 g (51 %) of 14-[[4-methylbenzenesulfonyl]oxy]-3,6,9,12-tetraoxatetradecan-1-ol as yellow oil.
46%	With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;	The title compound (6.1 g, 46%) was furnished as a colorless oil. It was prepared from 3,6,9,12-tetraoxatetradecane-1,14-diol (8.0 g, 33.57 mmol) following the procedure outlined for Example 2, Step 1. 1H NMR (400 MHz, CDCl3): δ 7.80 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 4.16 (t, J = 4.8 Hz,, 2H), 3.72 - 3.58 (m, 18H), 2.45 (s, 3H).
43%	With N-Trimethylamine hydrochloride; triethylamine; In dichloromethane; for 18h;	A solution of pentaethylene glycol (35g, 147mmol), TEA (41mL, 294mmol) and trimethylamine-HCl (1.4g, 14.7mmol) in CH2C12 (600mL) was treated with tosyl chloride (29.4g, 154mmol). After stirring (18h) the reaction mixture was washed with H20-brine (1 :1), dried (MgS04), filtered, concentrated and subjected to chromatography to yield 82 (24.6g, 43%) as a pale yellow oil. Rf 0.8 (10% CH30H-CH2C12).
43%	With N-Trimethylamine hydrochloride; triethylamine; In dichloromethane; for 18h;	A solution of pentaethylene glycol (35g, 147mmol), TEA (41mL, 294mm ol) and trimethylamine-HCl (1.4g, 14.7mmol) in CH2CI2 (600mL) was treated with tosyl chloride (29.4g, 154mmol). After stirring (18h) the reaction mixture was washed with EbO-brine (1 : 1), dried (MgS04), filtered, concentrated and subjected to chromatography to yield 82 (24.6g, 43%) as a pale yellow oil. Rf 0.8 (10% CH3OH-CH2CI2).
43%	With N-Trimethylamine hydrochloride; triethylamine; In dichloromethane; for 18h;	A solution of pentaethylene glycol (35g, 147mmol), TEA (41mL, 294mmol) and trimethylamine-HCl (1.4g, 14.7mmol) in CH2CI2 (600mL) was treated with tosyl chloride(29.4g, 154mmol). After stirring (18h) the reaction mixture was washed with EhO-brine (1 : 1), dried (MgS04), filtered, concentrated and subjected to chromatography to yield 82 (24.6g, 43%) as a pale yellow oil. Rf 0.8 (10% CH3OH-CH2CI2).
43%	With N-Trimethylamine hydrochloride; triethylamine; In dichloromethane; for 18h;	A solution of pentaethylene glycol (35g, 147mmol), TEA (41mL, 294mmol) and trimethylamine-HCl (1.4g, 14.7mmol) in CH2Cl2 (600mL) was treated with tosyl chloride (29.4g, 154mmol). After stirring (18h) the reaction mixture was washed with H2O-brine (1:1), dried (MgSO4), filtered, concentrated and subjected to chromatography to yield 82 (24.6g, 43%) as a pale yellow oil. Rf 0.8 (10% CH3OH-CH2Cl2).
42%	With triethylamine;	To a stirred solution of 3,6,9,12-tetraoxatetradecane-1,14-diol (70 g, 293.8 mmol) in DCM (500 mL) was added TEA (29.7 g, 293.8 mmol) followed by the addition of a solution of 4- methylbenzene-1-sulfonyl chloride (56.0 g, 293.8 mmol) in DCM (500 mL) over 30 min at room temperature under nitrogen atmosphere. The resulting solution was stirred for an additional 16 h at room temperature. Upon completion, the resulting solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, eluted with EtOAc to afford 14-[(4-methylbenzenesulfonyl)oxy]-3,6,9,12-tetraoxatetradecan-1-ol (48 g, 42%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) d 7.81 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 4.17 (t, J = 4.9 Hz, 2H), 3.80-3.56 (m, 18H), 2.50 (d, J = 4.4 Hz, 1H), 2.46 (s, 3H) LC/MS (ESI, m/z): [(M + 1)]+ = 393.00
38%	With potassium iodide; silver(I) oxide; In dichloromethane; at 0 - 20℃; for 16h;	To a solution of 3,6,9,12-tetraoxatetradecan-1,14-diol (0.50 g, 2.1 mmol), potassium iodide (69 mg, 0.42 mmol), and silver oxide (48 mg, 0.21 mmol) in methylene chloride (50 ml) was added p-toluenesulfonyl chloride (0.36 g, 1.9 mmol) at 0 C., and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was purified by preparative TLC (methylene chloride:methanol=10:1) to give Compound (p-2) (0.31 g, 38% yield). (1171) 1H-NMR (CDCl3, 400 MHz) δ: 7.80 (d, J=8.4 Hz, 2H), 7.34 (d, J=8.4 Hz, 2H), 4.17-4.15 (m, 2H), 3.71-3.60 (m, 19H), 2.45 (s, 3H).
	With triethylamine; In tetrahydrofuran;	FIGURE 36 shows the synthetic scheme used to obtain IBA-GN3. Pentaethylene glycol was treated with tosyl chloride in the presence of base to give the mono-tosylated alcohol, which was then treated with sodium azide at elevated temperature to give the azidoalcohol. This compound was then oxidized using Jones reagent, then reduced with Palladium on carbon under hydrogen atmosphere to give a carboxylic acid-amine. Separately, indole butyric acid was treated with N-hydroxysuccinimide, EDC, and DIPEA to give the NHS-ester indole, which was then reacted with the above carboxylic acid-amine. The product was again reacted with N-hydroxysuccinimide, EDC, and DIPEA to give a NHS ester. This NHS ester was reacted with NH2-GN3, which was prepared as described previously. The subsequent amide was deprotected with NaOMe in MeOH to give compound IBA-GN3.
	With sodium hydroxide; In tetrahydrofuran; water monomer; at 0 - 20℃; for 2h;	General procedure: Tetraethylene glycol (10.0g, 51.5mmol) was dissolved in tetrahydrofuran (30mL) at 0C. An aqueous solution of sodium hydroxide (0.3g, 7.7mmol) and TsCl (1.0g, 5.2mmol) were added to the reaction solution, stirred at 0C for 5min, and then stirred at room temperature for 2h. After the completion of the reaction, the reaction solution was filtered, and the filter cake was rinsed with dichloromethane. The filtrate was concentrated and washed twice with 10% NaHCO3 solution. The organic phase was concentrated and dried to obtain 1.7g of a colorless oil V-1 with a yield of 93%.
	With sodium hydroxide; In tetrahydrofuran; water monomer; at 0 - 20℃; for 2h;	General procedure: Tetraethylene glycol (10.0g, 51.5mmol) was dissolved in tetrahydrofuran (30mL) at 0C. An aqueous solution of sodium hydroxide (0.3g, 7.7mmol) and TsCl (1.0g, 5.2mmol) were added to the reaction solution, stirred at 0C for 5min, and then stirred at room temperature for 2h. After the completion of the reaction, the reaction solution was filtered, and the filter cake was rinsed with dichloromethane. The filtrate was concentrated and washed twice with 10% NaHCO3 solution. The organic phase was concentrated and dried to obtain 1.7g of a colorless oil V-1 with a yield of 93%.

Reference： [1]Israel Journal of Chemistry,2016,vol. 56,p. 249 - 256
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[8]Bioorganic Chemistry,2020,vol. 96
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[12]Patent: CN110204532,2019,A .Location in patent: Paragraph 0044-0045; 0055-0057
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4
[ 3588-80-5 ]
[ 155130-15-7 ]
2-[2-(2-{2-[2-(5-methoxy-naphthalen-1-yloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethanol [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 676 - 686

5
[ 83-56-7 ]
[ 155130-15-7 ]
1,5-bis[2-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]naphthalene [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 676 - 686
[2]Journal of Materials Chemistry C,2018,vol. 6,p. 8453 - 8459
[3]Chemical Communications,2019,vol. 55,p. 6169 - 6172

6
[ 155130-15-7 ]
1-[2-(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-5-methoxy-naphthalene [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 676 - 686

7
[ 155130-15-7 ]
2-[2-(2-{2-[2-(5-methoxy-naphthalen-1-yloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethylamine [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 676 - 686

8
[ 155130-15-7 ]
toluene-4-sulfonic acid 2-[2-(2-{2-[2-(5-methoxy-naphthalen-1-yloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl ester [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 676 - 686

9
[ 155130-15-7 ]
[ 872164-31-3 ]

Reference： [1]Macromolecules,2005,vol. 38,p. 676 - 686
[2]Chemical Communications,2019,vol. 55,p. 6169 - 6172

10
[ 155130-15-7 ]
1,5-bis-[2-(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-naphthalene [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 676 - 686

11
[ 155130-15-7 ]
2-{2-[2-(2-{2-[2-(5-methoxy-naphthalen-1-yloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl}-6-propyl-pyrrolo[3,4-<i>f</i>]isoindole-1,3,5,7-tetraone [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 676 - 686

12
[ 155130-15-7 ]
C₄₄H₆₀O₁₆S₂ [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 676 - 686
[2]Chemical Communications,2019,vol. 55,p. 6169 - 6172

13
[ 155130-15-7 ]
2,6-bis-{2-[2-(2-{2-[2-(5-methoxy-naphthalen-1-yloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl}-pyrrolo[3,4-<i>f</i>]isoindole-1,3,5,7-tetraone [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 676 - 686

14
[ 155130-15-7 ]
C₅₆H₆₄N₄O₁₈ [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 676 - 686

15
[ 155130-15-7 ]
[ 852806-22-5 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 3261 - 3263

16
[ 155130-15-7 ]
[ 852806-24-7 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 3261 - 3263

17
[ 155130-15-7 ]
[ 852806-26-9 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 3261 - 3263

18
[ 155130-15-7 ]
C₄₂H₅₀O₈ [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 3261 - 3263

19
[ 155130-15-7 ]
C₁₇H₂₇O₆S₄⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2004,p. 806 - 807

20
[ 155130-15-7 ]
[ 155130-05-5 ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 3255 - 3278

21
[ 155130-15-7 ]
C₄₇H₆₁N₃O₁₂S⁽²⁺⁾*2I^(1-) [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 3255 - 3278

22
[ 155130-15-7 ]
C₄₇H₆₁N₃O₁₂S⁽²⁺⁾*2ClO₄^(1-) [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 3255 - 3278

23
[ 155130-15-7 ]
C₄₇H₆₁N₃O₁₂S⁽²⁺⁾*2BF₄^(1-) [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 3255 - 3278

24
[ 155130-15-7 ]
[ 259796-30-0 ]

Reference： [1]Helvetica Chimica Acta,1999,vol. 82,p. 2186 - 2200

25
[ 155130-15-7 ]
[ 259796-32-2 ]

Reference： [1]Helvetica Chimica Acta,1999,vol. 82,p. 2186 - 2200

26
[ 155130-15-7 ]
17-amino-1-[(4,4'-dimethoxytrityl)oxy]methyl}-3,6,9,12,15-pentaoxaheptadecan-1-ol [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1999,vol. 82,p. 2186 - 2200

27
[ 155130-15-7 ]
2-{18-[(4,4'-dimethoxytrityl)oxy]-17-hydroxy-3,6,9,12,15-pentaoxaoctadec-1-yl}-1H-isoindole-1,3(2H)-dione [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1999,vol. 82,p. 2186 - 2200

28
[ 155130-15-7 ]
N-{18'-[(4,4'-dimethoxytrityl)oxy]-17'-hydroxy-3',6',9',12',15'-pentaoxaoctadec-1'-yl}dipyrido[3,2-a:2',3'-c]phenazine-11-carboxamide [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1999,vol. 82,p. 2186 - 2200

29
[ 155130-15-7 ]
N-{18'-[(4,4'-dimethoxytrityl)oxy]-17'-hydroxy-3',6',9',12',15'-pentaoxaoctadec-1'-yl}dipyrido[3,2-a:2',3'-c]phenazine-11-carboxamide 17'-(2-cyanoethyl diisopropylphosphoramidite) [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1999,vol. 82,p. 2186 - 2200

30
[ 442651-96-9 ]
[ 155130-15-7 ]
[ 1206101-93-0 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 5941 - 5947

31
[ 110-87-2 ]
[ 155130-15-7 ]
[ 1549752-65-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridinium p-toluenesulfonate; In dichloromethane; for 3h;Reflux;	14-(Tetrahydro-2H-pyran-2-yloxy)-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate (27) To a solution of 26 (2.613 g, 6.66 mmol) in DCM (100 mL) were added pyridinium p-toluenesulfonate (0.335 g, 1.33 mmol) and 2,3-dihydro-2H-pyran (0.91 mL, 9.99 mmol). The resulting mixture was refluxed for 3 h. After cooling the solution was concentrated under vacuum, poured into ice-water, and extracted with DCM. The combined organic layers were washed with water and brine, dried over MgSO4, filtered, and concentrated to give a yellow oil. The crude product was purified via silica flash chromatography using 4:1 EtOAc/Hex as an eluent, furnishing 27 (2.91 g, 92%): 1H NMR (300 MHz, CDCl3) δ 7.79 (d, J=8.2 Hz, 2H), 7.33 (d, J=8.2 Hz, 2H), 4.67-4.57 (m, 1H), 4.19-4.11 (m, 2H), 3.93-3.78 (m, 2H), 3.71-3.54 (m, 18H), 2.44 (s, 3H), 1.92-1.41 (m, 6H).
79%	With pyridinium p-toluenesulfonate; In dichloromethane; at 20℃; for 16h;	Into a 250-mL round-bottom flask, was placed 14-[(4-methylbenzenesulfonyl)oxy]- 3,6,9,12-tetraoxatetradecan-1-ol (9.22 g, 23.493 mmol, 1 equiv) in dichloromethane (150 mL), to which was added DHP (2.17 g, 25.798 mmol, 1.10 equiv) and PPTS (1.18 g, 4.696 mmol, 0.20 equiv) in sequence. The resulting mixture was stirred for 16 hr at room temperature. The mixture was quenched by 100 mL water and extracted with ethyl acetate (50 mL x 3). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (3/2). This resulted in 8.84 g (79%) of the title compound as a light yellow oil. MS (ES+): m/z 499.10 [MNa+]
12.5 g	With pyridinium p-toluenesulfonate; In dichloromethane; at 0 - 25℃; for 16h;	To a solution of 2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethyl 4- methylbenzenesulfonate (13 g, 33.12 mmol, 1 eq) in dichloromethane (100 mL) was added pyridine 4-methylbenzenesulfonate (416 mg, 1.66 mmol, 0.05 eq) and 3,4-dihydro-2H-pyran (3.34 g, 39.75 mmol, 3.63 mL, 1.2 eq) at 0C. Then the mixture was stirred at 25 C for 16 hours. The mixture was filtrated to get the filtrate. The filtrate was quenched by water (300 mL) and then diluted with dichloromethane (500 mL) and extracted with dichloromethane (500 mL x 2). The combined organic layers were washed with brine (300 mL), dried over, filtered and concentrated under reduced pressure to give a residue. The residue was purified by chromatography on silica gel (petroleum ether /ethyl acetate=3:l) to afford 2-[2-[2-[2-(2- tetrahydropyran-2-yloxyethoxy)ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate (12.5 g, 26.23 mmol) as yellow oil.

Reference： [1]Patent: US2014/31559,2014,A1 .Location in patent: Paragraph 0276
[2]Patent: WO2021/77010,2021,A1 .Location in patent: Paragraph 00563; 00564
[3]Patent: WO2019/195609,2019,A2 .Location in patent: Paragraph 001250-001251

32
[ 155130-15-7 ]
[ 1549752-74-0 ]

Reference： [1]Patent: US2014/31559,2014,A1

33
[ 155130-15-7 ]
2-(14-(4-isocyanatophenoxy)-3,6,9,12-tetraoxatetradecyloxy)tetrahydro-2H-pyran [ No CAS ]

Reference： [1]Patent: US2014/31559,2014,A1

34
[ 155130-15-7 ]
[ 1549752-89-7 ]

Reference： [1]Patent: US2014/31559,2014,A1

35
[ 155130-15-7 ]
[ 1549750-77-7 ]

Reference： [1]Patent: US2014/31559,2014,A1

36
[ 155130-15-7 ]
[ 1549750-84-6 ]

Reference： [1]Patent: US2014/31559,2014,A1

37
[ 119301-59-6 ]
[ 155130-15-7 ]
[ 1585154-10-4 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2170 - 2173

38
[ 155130-15-7 ]
14-azido-3,6,9,12-tetraoxatetradecan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With Caswell No. 744A; In N,N-dimethyl-formamide; at 80℃; for 12h;	To a mixture of <strong>[155130-15-7]2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate</strong> (4.50 g, 11.5 mmol) in DMF (30 mL) was added sodium azide (1.86 g, 28.6 mmol). Then the reaction mixture was stirred at 80 C. for 12 h. On completion, the reaction mixture was diluted with water (30 mL) and extracted with a mixture of dichloromethane and methanol (10:1, 3×30 mL). The organic layer was concentrated in vacuo to give the title compound (3.00 g, 99% yield) as a yellowish oil. LC-MS (ESI+) m/z 264.1 (M+H)+.
94%	With Caswell No. 744A; In ethanol; water monomer; at 80℃; for 16h;	A solution of <strong>[155130-15-7]14-[(4-methylbenzenesulfonyl)oxy]-3,6,9,12-tetraoxatetradecan-1-ol</strong> (44 g, 112.1 mmol) and NaN3 (29.2 g, 448.5 mmol) in EtOH (300 mL) and H2O (300 mL) was stirred for 16 h at 80 oC under nitrogen atmosphere. Upon completion, the resulting solution was concentrated under reduced pressure to remove EtOH. The residue was diluted with water (200 mL) and extracted with EtOAc (4 x 400 mL). The combined organic layers was washed with brine (500 mL) and dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, eluted with 5% methanol in dichloromethane to afford 14-azido-3,6,9,12-tetraoxatetradecan-1-ol (27.7 g, 94%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) d 3.71 (t, J = 4.5 Hz, 2H), 3.66 (s, 14H), 3.60 (t, J = 4.5 Hz, 2H), 3.38 (t, J = 5.1 Hz, 2H), 2.65 (br s, 1H). LC/MS (ESI, m/z): [(M + 1)]+ = 264.00
	With Caswell No. 744A; In N,N-dimethyl-formamide;Heating;	FIGURE 36 shows the synthetic scheme used to obtain IBA-GN3. Pentaethylene glycol was treated with tosyl chloride in the presence of base to give the mono-tosylated alcohol, which was then treated with sodium azide at elevated temperature to give the azidoalcohol. This compound was then oxidized using Jones reagent, then reduced with Palladium on carbon under hydrogen atmosphere to give a carboxylic acid-amine. Separately, indole butyric acid was treated with N-hydroxysuccinimide, EDC, and DIPEA to give the NHS-ester indole, which was then reacted with the above carboxylic acid-amine. The product was again reacted with N-hydroxysuccinimide, EDC, and DIPEA to give a NHS ester. This NHS ester was reacted with NH2-GN3, which was prepared as described previously. The subsequent amide was deprotected with NaOMe in MeOH to give compound IBA-GN3.

	With Caswell No. 744A; In N,N-dimethyl-formamide; at 100℃; for 12h;	General procedure: V-1 (1.7g, 4.8mmol) was dissolved in DMF solution, NaN3 (0.5g, 7.2mmol) was added, and the reaction was heated and stirred at 100C. After 12h, H2O was added to the reaction solution to quench the reaction, and then DCM was added and extracted three times. The organic phases were combined and spin-dried to obtain 1.1g of light yellow oily substance V-5, which was directly subjected to the next reaction without purification.
	With Caswell No. 744A; In N,N-dimethyl-formamide; at 100℃; for 12h;	General procedure: V-1 (1.7g, 4.8mmol) was dissolved in DMF solution, NaN3 (0.5g, 7.2mmol) was added, and the reaction was heated and stirred at 100C. After 12h, H2O was added to the reaction solution to quench the reaction, and then DCM was added and extracted three times. The organic phases were combined and spin-dried to obtain 1.1g of light yellow oily substance V-5, which was directly subjected to the next reaction without purification.

Reference： [1]Patent: WO2021/72269,2021,A1 .Location in patent: Page/Page column 189
[2]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 2097; 2099
[3]Patent: WO2020/10210,2020,A1 .Location in patent: Paragraph 00674; 00677
[4]Angewandte Chemie - International Edition,2017,vol. 56,p. 10691 - 10695
Angew. Chem.,2017,vol. 129,p. 10831 - 10835
[5]Journal of Materials Chemistry B,2014,vol. 2,p. 3741 - 3744
[6]Patent: WO2019/199634,2019,A1 .Location in patent: Page/Page column 72
[7]Bioorganic and Medicinal Chemistry,2022,vol. 61
[8]Bioorganic and Medicinal Chemistry,2022,vol. 61

39
[ 155130-15-7 ]
[ 34188-11-9 ]

Reference： [1]Journal of Materials Chemistry B,2014,vol. 2,p. 3741 - 3744
[2]Patent: US2019/192668,2019,A1

40
[ 155130-15-7 ]
C₄₈H₅₆O₁₂ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 6925 - 6934

41
[ 155130-15-7 ]
C₄₈H₅₆O₁₂*C₁₂H₁₄N₂⁽²⁺⁾*2F₆P^(1-) [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 6925 - 6934

42
[ 155130-15-7 ]
C₄₈H₆₂O₁₆S₂ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 6925 - 6934

43
[ 607-61-4 ]
[ 155130-15-7 ]
C₃₄H₅₀O₁₂ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 6925 - 6934

44
[ 155130-15-7 ]
C₃₀H₅₁BrO₇ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 12751 - 12755
Angew. Chem.,2014,vol. 126,p. 12965 - 12969,5
[2]Israel Journal of Chemistry,2016,vol. 56,p. 249 - 256

45
[ 155130-15-7 ]
C₂₅H₄₄O₆S [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 12751 - 12755
Angew. Chem.,2014,vol. 126,p. 12965 - 12969,5
[2]Israel Journal of Chemistry,2016,vol. 56,p. 249 - 256

46
[ 155130-15-7 ]
C₂₁H₃₃BrO₇ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 12751 - 12755
Angew. Chem.,2014,vol. 126,p. 12965 - 12969,5
[2]Israel Journal of Chemistry,2016,vol. 56,p. 249 - 256

47
[ 106-41-2 ]
[ 155130-15-7 ]
C₁₆H₂₅BrO₆ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 12751 - 12755
Angew. Chem.,2014,vol. 126,p. 12965 - 12969,5
[2]Israel Journal of Chemistry,2016,vol. 56,p. 249 - 256
[3]Patent: US2018/125821,2018,A1 .Location in patent: Paragraph 1036

48
[ 155130-15-7 ]
C₂₅H₃₁⁽¹⁸⁾FN₂O₅ [ No CAS ]

Reference： [1]ACS Chemical Neuroscience,2016,vol. 7,p. 897 - 911

49
[ 155130-15-7 ]
t-butyl (4-(6-((14-hydroxy-3,6,9,12-tetraoxatetradecyl)oxy)quinolin-2-yl)phenyl)carbamate [ No CAS ]

Reference： [1]ACS Chemical Neuroscience,2016,vol. 7,p. 897 - 911

50
[ 155130-15-7 ]
14-((2-(4-((t-Boc)amino)phenyl)quinolin-6-yl)oxy)-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate [ No CAS ]

Reference： [1]ACS Chemical Neuroscience,2016,vol. 7,p. 897 - 911

51
[ 155130-15-7 ]
4-(6-((14-fluoro-3,6,9,12-tetraoxatetradecyl)oxy)quinolin-2-yl)aniline [ No CAS ]

Reference： [1]ACS Chemical Neuroscience,2016,vol. 7,p. 897 - 911

52
[ 155130-15-7 ]
C₃₀H₃₉⁽¹⁸⁾FN₂O₇ [ No CAS ]

Reference： [1]ACS Chemical Neuroscience,2016,vol. 7,p. 897 - 911

53
[ 577967-89-6 ]
[ 155130-15-7 ]
14-((2-chloroquinolin-6-yl)oxy)-3,6,9,12-tetraoxatetradecan-1-ol [ No CAS ]

Reference： [1]ACS Chemical Neuroscience,2016,vol. 7,p. 897 - 911

54
[ 155130-15-7 ]
N-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-3-[ethyl(oxan-4-yl)amino]-5-[4-[(14-hydroxy-3,6,9,12-tetraoxatetradecan-1-yl)oxy]phenyl]-2-methylbenzamide [ No CAS ]

Reference： [1]Patent: WO2017/11590,2017,A1

55
[ 155130-15-7 ]
N-[[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl]-3-[ethyl(oxan-4-yl)amino]-5-[4[(14-hydroxy-3,6,9,12-tetraoxatetradecan-1-yl)oxy]phenyl]-2-methylbenzamide [ No CAS ]

Reference： [1]Patent: WO2017/11590,2017,A1

56
[ 155130-15-7 ]
1-[4-[3-([[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl]carbamoyl)-5-[ethyl(oxan-4-yl)amino]-4-methylphenyl]phenyl]-1,4,7,10,13-pentaoxapentadecan-15-yl 4-methylbenzene-1-sulfonate [ No CAS ]

Reference： [1]Patent: WO2017/11590,2017,A1

57
[ 155130-15-7 ]
[ 269409-70-3 ]
1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,4,7,10,13-pentaoxapentadecan-15-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 16h;	Into a 250-mL round-bottom flask, was placed a solution of 14-[[4-methylbenzenesulfonyl]oxy]-3,6,9,12-tetraoxatetradecan-1-ol (2.0 g, 5.10 mmol, 1.00 equiv) in N,N-dimethylformamide (150 mL), potassium carbonate (2.2 g, 15.92 mmol, 3.00 equiv), 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1.5 g, 6.82 mmol, 1.50 equiv). The resulting solution was stirred for 16 h at 60C in an oil bath. The reaction was then quenched by the addition of water (100 mL) and extracted with ethyl acetate (50 mL x 3). The combined organic layers were washed with brine (80 mL x 2), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1/1). This resulted in 1.2 g (53%) of 1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,4,7,10,13-pentaoxapentadecan-15-ol as yellow oil.

Reference： [1]Patent: WO2017/11590,2017,A1 .Location in patent: Paragraph 00431

58
[ 155130-15-7 ]
Cl^(1-)*C₃₈H₅₀N₅O₇⁽¹⁺⁾ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 10691 - 10695
Angew. Chem.,2017,vol. 129,p. 10831 - 10835

59
[ 155130-15-7 ]
Cl^(1-)*C₄₇H₆₄N₅O₁₃⁽¹⁺⁾ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 10691 - 10695
Angew. Chem.,2017,vol. 129,p. 10831 - 10835

60
[ 155130-15-7 ]
1,5-bis[2-(2-{2-[2-(2-bromoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]naphthalene [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2018,vol. 6,p. 8453 - 8459

61
[ 155130-15-7 ]
C₅₂H₅₆N₂O₁₂S [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2018,vol. 6,p. 8453 - 8459

62
[ 155130-15-7 ]
[ 129-64-6 ]
exo,exo-bis(2-(2′-(2″-(2’’’-(2’’’’-tosyloxyethoxy)ethoxy)ethoxy)ethoxy)ethyl) bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate [ No CAS ]

Reference： [1]Macromolecules,2019,vol. 52,p. 1371 - 1388

63
[ 155130-15-7 ]
[ 957205-14-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tetrabutylammomium bromide; potassium bromide; In acetone; at 80℃; for 10h;	A solution of Compound (p-2) (0.13 g, 0.32 mmol), potassium bromide (0.11 g, 0.95 mmol), and tetrabutylammonium bromide (0.10 g, 0.32 mmol) in acetone (10 ml) was stirred at 80 C. for 10 hours. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride:methanol=20:1) to give Compound (p-3) (83 mg, 87% yield). (1174) 1H-NMR (CDCl3, 400 MHz) δ: 3.83-3.79 (m, 2H), 3.74-3.70 (m, 2H), 3.70-3.62 (m, 8H), 3.62-3.61 (m, 2H), 3.49-3.46 (m, 2H), 2.96 (br, 1H), 1.75 (s, 4H).

Reference： [1]Patent: US2019/16711,2019,A1 .Location in patent: Paragraph 1172-1174

64
[ 56683-55-7 ]
[ 155130-15-7 ]
C₃₂H₄₆O₁₄S [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 8034 - 8038
Angew. Chem.,2019,vol. 131,p. 8118 - 8122,5

65
[ 60835-75-8 ]
[ 155130-15-7 ]
C₃₄H₅₀O₁₅S [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 8034 - 8038
Angew. Chem.,2019,vol. 131,p. 8118 - 8122,5

66
C₅₆H₈₆N₄O₁₁ [ No CAS ]
[ 155130-15-7 ]
C₆₆H₁₀₆N₄O₁₆ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 8034 - 8038
Angew. Chem.,2019,vol. 131,p. 8118 - 8122,5

67
[ 155130-15-7 ]
C₄₆H₅₄N₂O₁₄ [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 6169 - 6172

68
[ 155130-15-7 ]
2,2,5-trimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azanonadecan-19-yl methanesulfonate [ No CAS ]