(S)-2-[(S)-2-Amino-4-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-butyrylamino]-propionic acid benzyl ester

Base Information

• Chemical Name: (S)-2-[(S)-2-Amino-4-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-butyrylamino]-propionic acid benzyl ester
• CAS No.: 676602-53-2
• Molecular Formula: C₂₈H₃₉N₃O₁₁S
• Molecular Weight: 625.697
• Mol file: 676602-53-2.mol

Synonyms:

Chemical Property of (S)-2-[(S)-2-Amino-4-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-butyrylamino]-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(S)-2-Amino-4-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-butyrylamino]-propionic acid benzyl ester

There total 6 articles about (S)-2-[(S)-2-Amino-4-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-butyrylamino]-propionic acid benzyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-tert-butoxycarbonyl-S-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-homocysteinyl-L-alanine benzyl ester (613244-61-4) → (S)-2-[(S)-2-Amino-4-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-butyrylamino]-propionic acid benzyl ester (676602-53-2)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane;

DOI:10.1039/b311583f

Reference yield:

L-alanine benzyl ester hydrochloride (5557-81-3,5557-83-5,34404-37-0) → (S)-2-[(S)-2-Amino-4-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-butyrylamino]-propionic acid benzyl ester (676602-53-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / PyBOP; DIPEA / dimethylformamide

2: 98 percent / PBu₃ / CHCl₃; aq. methanol

3: 90 percent / aq. Na₂CO₃; TBAHS / ethyl acetate

4: 87 percent / Zn; Et₃N / 3 h / ultrasonic bath

5: aq. TFA; TESH / CH₂Cl₂

With triethylsilane; tributylphosphine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; zinc; In methanol; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/b311583f

Reference yield:

3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide (67124-60-1) → (S)-2-[(S)-2-Amino-4-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-butyrylamino]-propionic acid benzyl ester (676602-53-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / aq. Na₂CO₃; TBAHS / ethyl acetate

2: 87 percent / Zn; Et₃N / 3 h / ultrasonic bath

3: aq. TFA; TESH / CH₂Cl₂

With triethylsilane; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; triethylamine; trifluoroacetic acid; zinc; In dichloromethane; ethyl acetate;

DOI:10.1039/b311583f

upstream raw materials:

N-tert-butoxycarbonyl-S-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-homocysteinyl-L-alanine benzyl ester

L-alanine benzyl ester hydrochloride

3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide

Boc-Hcy-Ala-OBn