[ CAS No. 123639-61-2 ]

Name: 123639-61-2|Fmoc-Glu(OBzl)-OH|97%
Brand: Ambeed
SKU: A138373
Price: 5.0 USD
Availability: InStock
Rating: 91 (26 reviews)

{[proInfo.proName]} (Synonyms:Fmoc-Glu(OBzl)-OH) ,{[proInfo.pro_purity]}

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

2D 3D

Structure of 123639-61-2 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 100K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 123639-61-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 123639-61-2 ]

SDS Specification

Alternatived Products of [ 123639-61-2 ]

Product Details of [ 123639-61-2 ]

CAS No. :	123639-61-2	MDL No. :	MFCD00065642
Formula :	C₂₇H₂₅NO₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HJJURMMMGPQIQP-DEOSSOPVSA-N
M.W :	459.49	Pubchem ID :	13966932
Synonyms :	Fmoc-Glu(OBzl)-OH

Calculated chemistry of [ 123639-61-2 ]

Physicochemical Properties

Num. heavy atoms :	34
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.22
Num. rotatable bonds :	12
Num. H-bond acceptors :	6.0
Num. H-bond donors :	2.0
Molar Refractivity :	125.36
TPSA :	101.93 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.92
Log Po/w (XLOGP3) :	4.36
Log Po/w (WLOGP) :	4.35
Log Po/w (MLOGP) :	3.17
Log Po/w (SILICOS-IT) :	4.35
Consensus Log Po/w :	3.83

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-5.04
Solubility :	0.00424 mg/ml ; 0.00000922 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.22
Solubility :	0.000279 mg/ml ; 0.000000608 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-7.81
Solubility :	0.00000712 mg/ml ; 0.0000000155 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	4.4

Safety of [ 123639-61-2 ]

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 [ 123639-61-2 ]

* 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 [ 123639-61-2 ]
Downstream synthetic route of [ 123639-61-2 ]

[ 123639-61-2 ] Synthesis Path-Upstream 1~2

1
[ 123639-61-2 ]
[ 84793-07-7 ]

Reference： [1] Journal of the Chemical Society. Perkin Transactions 1, 2002, # 8, p. 1042 - 1049

2
[ 57-88-5 ]
[ 123639-61-2 ]

Reference： [1] Patent: EP804456, 2002, B1,

[ 123639-61-2 ] Synthesis Path-Downstream 1~68

1
[ 123639-61-2 ]
[ 123622-36-6 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 721 - 728

2
[ 123639-61-2 ]
[ 35661-40-6 ]
[ 86060-88-0 ]
(S)-4-[(S)-1-((S)-1-Carbamoyl-3-methyl-butylcarbamoyl)-2-phenyl-ethylcarbamoyl]-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 8190 - 8197

3
[ 914927-66-5 ]
[ 123639-61-2 ]
[ 86060-88-0 ]
(S)-4-[(S)-1-((S)-1-Carbamoyl-3-methyl-butylcarbamoyl)-2-(4-sulfamoylmethyl-phenyl)-ethylcarbamoyl]-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 8190 - 8197

4
[ 914927-72-3 ]
[ 123639-61-2 ]
[ 86060-88-0 ]
(S)-4-{(S)-1-((S)-1-Carbamoyl-3-methyl-butylcarbamoyl)-2-[4-(difluoro-sulfamoyl-methyl)-phenyl]-ethylcarbamoyl}-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 8190 - 8197

5
[ 123639-61-2 ]
[ 86060-88-0 ]
[ 916726-85-7 ]
(S)-4-((S)-1-((S)-1-Carbamoyl-3-methyl-butylcarbamoyl)-2-{4-[(2,2-dimethyl-propoxysulfonyl)-difluoro-methyl]-phenyl}-ethylcarbamoyl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 8190 - 8197

6
[ 905456-87-3 ]
[ 122889-11-6 ]
[ 123639-61-2 ]
[ 150009-58-8 ]
NovaSyn TG(R) Amino Resin (HL) loaded with 4-[2-(N-fluorenylmethoxycarbonyl-L-isoleucyloxy)-1-(trimethylsilyl)-ethyl]-phenoxy-acetic acid [ No CAS ]
C₁₅₉H₁₈₆N₁₂O₃₈ [ No CAS ]

Reference： [1]Carbohydrate Research,2006,vol. 341,p. 1597 - 1608

7
{2-[N'-(2-amino-ethyl)-N''-trifluoroacetyl-guanidino]-ethyl}-carbamic acid tert-butyl ester [ No CAS ]
[ 123639-61-2 ]
[ 879880-77-0 ]

Reference： [1]Chemistry - A European Journal,2006,vol. 12,p. 713 - 720

8
[ 930806-24-9 ]
[ 35661-60-0 ]
[ 123639-61-2 ]
[ 71989-31-6 ]
N-(fluorenyl-9-methoxycarbonyl)-L-phenylalanyl-L-leucyl-L-prolyl-L-(5-O-benzyl)-glutamyl-L-N⁴-(14-hydroxycarbonyl-3,6,9,12-tetra-oxa-tetradecyl)asparaginyl-L-(5-O-benzyl)-glutamic acid amide [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 6423 - 6436

9
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 123639-61-2 ]
[ 108-24-7 ]
[ 117872-75-0 ]
Fmoc-Phe(p-CH₂SO₃H)-OH [ No CAS ]
Fmoc-Asp(OBn)-(Wang resin) [ No CAS ]
N-acetyl-L-alanyl-L-(O-benzyl)-threonyl-L-(5-O-benzyl)-glutamyl-L-(p-sulfomethyl)phenylalanyl-L-(5-O-benzyl)-glutamyl-L-(p-sulfomethyl)phenylalanyl-L-leucyl-L-(4-O-benzyl)-aspartate [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 6423 - 6436

10
[ 123639-61-2 ]
(S)-4-{(S)-1-((S)-1-Carbamoyl-3-methyl-butylcarbamoyl)-2-[4-(difluoro-sulfo-methyl)-phenyl]-ethylcarbamoyl}-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 8190 - 8197

11
[ 123639-61-2 ]
cyclo-(-Arg[Pbf]GlyAsp[tBu]-D-PheGlu-) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2003,vol. 9,p. 2717 - 2725

12
[ 123639-61-2 ]
cyclo-(-Arg[Pbf]GlyAsp[tBu]-D-PheGlu[Bzl]-) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2003,vol. 9,p. 2717 - 2725

13
[ 123639-61-2 ]
[ 600153-19-3 ]

Reference： [1]Chemistry - A European Journal,2003,vol. 9,p. 2717 - 2725

14
[ 123639-61-2 ]
(S)-2-(6-{3-[(2S,5S,11S,14R)-14-Benzyl-11-carboxymethyl-5-(3-guanidino-propyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaaza-cyclopentadec-2-yl]-propionylamino}-hexanoylamino)-3-{2-[1-(4-iodo-phenyl)-meth-(E)-ylideneaminooxy]-acetylamino}-propionic acid [ No CAS ]

Reference： [1]Chemistry - A European Journal,2003,vol. 9,p. 2717 - 2725

15
[ 123639-61-2 ]
[ 84793-07-7 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 1042 - 1049

16
[ 123639-61-2 ]
[ 122350-66-7 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 1042 - 1049

17
[ 123639-61-2 ]
[ 467465-79-8 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 1042 - 1049

18
[ 123639-61-2 ]
Fmoc-Gln[Man(OAc)4]-OH [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 1042 - 1049

19
[ 123639-61-2 ]
[ 467465-71-0 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 1042 - 1049

20
[ 123639-61-2 ]
[ 467465-73-2 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 1042 - 1049

21
[ 123639-61-2 ]
[ 467465-75-4 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 1042 - 1049

22
[ 123639-61-2 ]
Fmoc-Gln[Lac(OAc)7]-OH [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 1042 - 1049

23
[ 123639-61-2 ]
[ 467465-77-6 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 1042 - 1049

24
[ 123639-61-2 ]
c(-Tyr(tBu)-Asp(OBzl)-Phe-Phe-Ser(tBu)-D-Ala-) [ No CAS ]

Reference： [1]Liebigs Annalen der Chemie,1993,p. 497 - 502

25
[ 123639-61-2 ]
c(-Tyr(Bzl)-Asp(OBzl)-Phe-Phe-Thr(tBu)-D-Ala-) [ No CAS ]

Reference： [1]Liebigs Annalen der Chemie,1993,p. 497 - 502

26
[ 123639-61-2 ]
H-Glu(OBn)-Phe-Phe-Gly-Leu-Nle-OBn [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 721 - 728

27
[ 123639-61-2 ]
FMOC-Glu(OBn)-Phe-Phe-Gly-Leu-Nle-OBn [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 721 - 728

28
[ 123639-61-2 ]
[ 123622-32-2 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 721 - 728

29
γ-benzyl glutamate [ No CAS ]
fluorenylmethyloxycarbonyl chloride [ No CAS ]
[ 123639-61-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In 1,4-dioxane; water;	EXAMPLE 83 N-alpha-(FMOC)-glutamic acid gamma-benzyl ester To a solution of gamma-benzyl glutamate (10 mmol) in 50 ml dioxane and 50 ml water is added triethylamine (25 mmol), followed by a solution of fluorenylmethyl chloroformate (11 mmol) in 50 ml dioxane. The mixture is vigorously stirred until the starting material is consumed. The solution is acidified to pH 2 with concentrated HCl, extracted with ethyl acetate (2*250 ml), washed with brine, dried with MgSO4 and evaporated. The product is used without purification.
	With triethylamine; In 1,4-dioxane; water;	EXAMPLE 36 N-alpha-(FMOC)-glutamic acid gamma-benzyl ester. To a solution of gamma-benzyl glutamate (10 mmol) in 50 ml dioxane and 50 ml water is added triethylamine (25 mmol), followed by a solution of fluorenylmethyl chloroformate (11 mmol) in 50 ml dioxane. The mixture is vigorously stirred until the starting material is consumed. The solution is acidified to pH 2 with concentrated HCl, extracted with ethyl acetate (2*250 ml), washed with brine, dried with MgSO4 and evaporated. The product is used without purification.
	With triethylamine; In 1,4-dioxane; water;	EXAMPLE 37 N-alpha-(FMOC)-glutamic acid gamma-benzyl ester To a solution of gamma-benzyl glutamate (10 mmol) in 50 ml dioxane and 50 ml water is added triethylamine (25 mmol), followed by a solution of fluorenylmethyl chloroformate (11 mmol) in 50 ml dioxane. The mixture is vigorously stirred until the starting material is consumed. The solution is acidified to pH 2 with concentrated HCl, extracted with ethyl acetate (2*250 ml), washed with brine, dried with MgSO4 and evaporated. The product is used without purification.

Reference： [1]Patent: US5886177,1999,A
[2]Patent: US5519134,1996,A
[3]Patent: US5714606,1998,A

Yield	Reaction Conditions	Operation in experiment
83%		EXAMPLE 5 Synthesis of Fmoc-glutamic Acid alpha-benzyl Ester Twenty-five g (0.105M) glutamic acid alpha-benzyl ester and 25 g Na2 CO4 was dissolved in 400 mL of water and 200 mL THF was added. 34 g (0.101M, 0.96 eq) Fmoc-OSu was added in small portions with stirring, and the pH was kept at about 9 by adding more Na2 CO3 as needed. After 1 hr, the reaction was poured into 500 mL of water and acidified with conc HCl. The white suspension was extracted with EtOAc, dried over Na2 SO4 and evaporated to a solid mass. This was dissolved in 500 mL hot EtOAc and 300 mL hexane was added. Overnight chilling, collection and air-drying gave 38.7 g (83% yield) of white crystals, mp 110-112. [a]d =-13.8. M/e (Rel. inten.): 460.2 (19), 363.4 (8), 345.4 (19), 307.2 (10), 289.2 (12), 238.2 (12), 191.2 (10), 178.2 (89), 165.1 (23), 154.1 (57), 136.1 (48). 1 H NMR (400 mHz), PPM: 1.9 (m, 1H), 2.2 (m, 1H), 2.4 (M, 2H), 4.1 (t, 1H), 4.4 (d, 2H), 4.43 (m, 1H), 5.1 (s, 2H), 5.6 (d, 1H), 7.3 (m, 9H), 7.5 (d, 2H), 7.7 (d, 2H), 9.4-9.6 (broad s, 1H). 13 C (100 mHz), PPM: 27.5, 30.0, 47.3, 53.5, 67.3, 67.7, 120.2, 125.0, 127.3, 128.5, 128.8, 129.2, 135.2, 141.5, 143.6, 143.9, 156.3, 171.4, 177.8. Anal. Calcd. for C27 H25 NO6: C, 70.57. H, 5.48. N, 3.05. Found: C, 69.71. H, 5.58. N, 2.88.
83%		EXAMPLE 5 Synthesis of Fmoc-glutamic acid alpha-benzyl ester Twenty-five g (0.105M) glutamic acid alpha-benzyl ester and 25 g Na2 CO4 was dissolved in 400 ml of water and 200 ml THF was added. 34 g (0.101M, 0.96 eq) Fmoc-OSu was added in small portions with stirring, and the pH was kept at about 9 by adding more Na2 CO3 as needed. After 1 hr, the reaction was poured into 500 ml of water and acidified with conc HCl. The white suspension was extracted with EtOAc, dried over Na2 SO4 and evaporated to a solid mass. This was dissolved in 500 ml hot EtOAc and 300 ml hexane was added. Overnight chilling, collection and air-drying gave 38.7 g (83% yield) of white crystals, mp 110-112. [a]d =-13.8. M/e (Rel. inten.): 460.2 (19), 363.4 (8), 345.4 (19), 307.2 (10), 289.2 (12), 238.2 (12), 191.2 (10), 178.2 (89), 165.1 (23), 154.1 (57), 136.1 (48). 1 H NMR (400 mHz), PPM: 1.9 (m, 1H), 2.2 (m, 1H), 2.4 (M, 2H), 4.1 (t, 1H), 4.4 (d, 2H), 4.43 (m, 1H), 5.1 (s, 2H), 5.6 (d, 1H), 7.3 (m, 9H), 7.5 (d, 2H), 7.7 (d, 2H), 9.4-9.6 (broad s, 1H). 13 C (100 mHz), PPM: 27.5, 30.0, 47.3, 53.5, 67.3, 67.7, 120.2, 125.0, 127.3, 128.5, 128.8, 129.2, 135.2, 141.5, 143.6, 143.9, 156.3, 171.4, 177.8. Anal. Calcd. for C27 H25 NO6: C, 70.57. H, 5.48. N, 3.05. Found: C, 69.71. H, 5.58. N, 2.88.
83%		EXAMPLE 5 Synthesis of Fmoc-glutamic acid alpha-benzyl ester Twenty-five g (0.105 M) glutamic acid alpha-benzyl ester and 25 g Na2CO4 was dissolved in 400 mL of water and 200 mL THF was added. 34 g (0.101 M, 0.96 eq) Fmoc-OSu was added in small portions with stirring, and the pH was kept at about 9 by adding more Na2CO3 as needed. After 1 hr, the reaction was poured into 500 mL of water and acidified with conc HCl. The white suspension was extracted with EtOAc, dried over Na2SO4 and evaporated to a solid mass. This was dissolved in 500 mL hot EtOAc and 300 mL hexane was added. Overnight chilling, collection and air-drying gave 38.7 g (83% yield) of white crystals, mp 110-112. [a]d= -13.8. M/e (Rel. inten.): 460.2 (19), 363.4 (8), 345.4 (19), 307.2 (10), 289.2 (12), 238.2 (12), 191.2 (10), 178.2 (89), 165.1 (23), 154.1 (57), 136.1 (48). 1H NMR (400 mHz), PPM: 1.9 (m, 1H), 2.2 (m, 1H), 2.4 (M, 2H), 4.1 (t, 1H), 4.4 (d, 2H), 4.43 (m, 1H), 5.1 (s, 2H), 5.6 (d, 1H), 7.3 (m, 9H), 7.5 (d, 2H), 7.7 (d, 2H), 9.4-9.6 (broad s, 1H). 13C (100 mHz), PPM: 27.5, 30.0, 47.3, 53.5, 67.3, 67.7, 120.2, 125.0, 127.3, 128.5, 128.8, 129.2, 135.2, 141.5, 143.6, 143.9, 156.3, 171.4, 177.8.

31
γ-benzyl glutamate [ No CAS ]
fluorenylmethyloxycarbonyl chloride [ No CAS ]
[ 57-88-5 ]
[ 123639-61-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In 1,4-dioxane; water;	EXAMPLE 106 N-alpha-(FMOC)-glutamic acid -gamma-benzyl ester (106) To a solution of gamma-benzyl glutamate (10 mmol) in 50 ml dioxane and 50 ml water is added triethylamine (25 mmol), followed by a solution of fluorenylmethyl chloroformate (11 mmol) in 50 ml dioxane. The mixture is vigorously stirred until the starting material is consumed. The solution is acidified to pH 2 with concentrated HCl, extracted with ethyl acetate (2 X 250 ml), washed with brine, dried with MgSO4 and evaporated. The product is used without purification.

Reference： [1]Patent: EP804456,2002,B1

32
[ 29022-11-5 ]
[ 123639-61-2 ]
[ 35661-40-6 ]
[ 3128-06-1 ]
[ 1036637-24-7 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 3413 - 3418

33
C₁₈H₁₆NO₄Pol [ No CAS ]
[ 126727-03-5 ]
[ 123639-61-2 ]
[ 86060-82-4 ]
[ 94744-50-0 ]
Ala-L-Glu(OBzl)-Leu-Aib-L-Lys(Z)-Leu [ No CAS ]

Reference： [1]Magnetic Resonance in Chemistry,2008,vol. 46,p. 955 - 961

34
[ 98946-18-0 ]
[ 123639-61-2 ]
[ 157108-58-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3652 - 3656

35
[ 123639-61-2 ]
[ 541-41-3 ]
C₃₀H₂₉NO₈ [ No CAS ]

Reference： [1]Synlett,2010,p. 1037 - 1042

36
[ 123639-61-2 ]
[ 1258792-62-9 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 6338 - 6341

37
H-Gly-2CT resin [ No CAS ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 123639-61-2 ]
[ 71989-31-6 ]
[ 117872-75-0 ]
[ 1415218-38-0 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 10185 - 10189,5
Angewandte Chemie,2012,vol. 124,p. 10332 - 10336,5

38
[ 35661-39-3 ]
C₂₄H₂₉NO₆ [ No CAS ]
[ 123639-61-2 ]
[ 71989-23-6 ]
(3S,7S,10S,13S)-3-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-7-(3-(benzyloxy)-3-oxopropyl)-13-sec-butyl-10-methyl-5,8,11-trioxo-1-phenyl-2,6,9,12-tetraazatetradecan-14-oic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		General procedure: The peptides were synthesized on an activated [44] 2-chlorotrityl chloride resin (1 g) which had been swelled in dry DCM for 30 min. The first Fmoc amino acid (4 equiv) was coupled to the resin manually using dry DCM (10 mL) and DIPEA (6 equiv) for 2 h under a N2 atmosphere. Resin substitution was then determined using the Fmoc UV assay. On 0.1 mM scale subsequent amino acids were also coupled manually using amino acid (0.20 mM, 2.5 mL), DIPEA (1 mM, 1.0 mL) and HBTU (0.50 mM, 1.0 mL) in DMF. The Fmoc group of amino acid was removed using 20% piperidine-DMF (3 × 10 mL) for 30 min and the next amino acid and sugar amino acid 1a/b were coupled on resin using the same condition. The excess reagents were washed with DMF (2 × 7 mL) and DCM (2 × 7 mL). Cleavage from resin was performed manually, using a cleavage mixture of TFA-DCM [5:95% (v/v), 3 × 10 mL] for 30 min. The crude compound was then purified using semi-preparative HPLC. All compounds were obtained in good yields.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 60,p. 144 - 154

39
[ 35661-39-3 ]
C₂₂H₃₁NO₈ [ No CAS ]
[ 123639-61-2 ]
[ 71989-23-6 ]
(2S,3S)-2-((2S)-2-((2S)-2-((3S)-3-amino-3-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)propanamido)-5-(benzyloxy)-5-oxopentanamido)propanamido)-3-methylpentanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		General procedure: The peptides were synthesized on an activated [44] 2-chlorotrityl chloride resin (1 g) which had been swelled in dry DCM for 30 min. The first Fmoc amino acid (4 equiv) was coupled to the resin manually using dry DCM (10 mL) and DIPEA (6 equiv) for 2 h under a N2 atmosphere. Resin substitution was then determined using the Fmoc UV assay. On 0.1 mM scale subsequent amino acids were also coupled manually using amino acid (0.20 mM, 2.5 mL), DIPEA (1 mM, 1.0 mL) and HBTU (0.50 mM, 1.0 mL) in DMF. The Fmoc group of amino acid was removed using 20% piperidine-DMF (3 × 10 mL) for 30 min and the next amino acid and sugar amino acid 1a/b were coupled on resin using the same condition. The excess reagents were washed with DMF (2 × 7 mL) and DCM (2 × 7 mL). Cleavage from resin was performed manually, using a cleavage mixture of TFA-DCM [5:95% (v/v), 3 × 10 mL] for 30 min. The crude compound was then purified using semi-preparative HPLC. All compounds were obtained in good yields.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 60,p. 144 - 154

40
[ 50-00-0 ]
[ 123639-61-2 ]
[ 1448903-47-6 ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 4509 - 4513

41
C₂₁H₂₆N₃O₅Pol [ No CAS ]
azido-4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-1-O-trifuoro-N-phenylimidate-D-galactopyranoside [ No CAS ]
[ 123639-61-2 ]
[ 71989-35-0 ]
[ 1138-80-3 ]
[ 507-09-5 ]
[ 55722-49-1 ]
C₇₄H₉₅N₇O₂₇ [ No CAS ]
C₇₄H₉₅N₇O₂₇ [ No CAS ]