(S)-methyl 2-((S)-3-(benzyloxy)-2-(benzyloxycarbonylamino)propanamido)-3-hydroxypropanoate

Base Information

• Chemical Name: (S)-methyl 2-((S)-3-(benzyloxy)-2-(benzyloxycarbonylamino)propanamido)-3-hydroxypropanoate
• CAS No.: 75893-22-0
• Molecular Formula: C₂₂H₂₆N₂O₇
• Molecular Weight: 430.458
• Mol file: 75893-22-0.mol

Synonyms:(S)-methyl 2-((S)-3-(benzyloxy)-2-(benzyloxycarbonylamino)propanamido)-3-hydroxypropanoate

Chemical Property of (S)-methyl 2-((S)-3-(benzyloxy)-2-(benzyloxycarbonylamino)propanamido)-3-hydroxypropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-methyl 2-((S)-3-(benzyloxy)-2-(benzyloxycarbonylamino)propanamido)-3-hydroxypropanoate

There total 3 articles about (S)-methyl 2-((S)-3-(benzyloxy)-2-(benzyloxycarbonylamino)propanamido)-3-hydroxypropanoate 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:

Z-Ser(Bzl)-OH (20806-43-3) + methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) → (S)-methyl 2-((S)-3-(benzyloxy)-2-(benzyloxycarbonylamino)propanamido)-3-hydroxypropanoate (75893-22-0)

Guidance literature:

With chloroformic acid ethyl ester; triethylamine; 1) THF, -10 deg C, 10 min 2) DMF, THF, 0 deg C, 3 h;

DOI:10.1248/cpb.28.2699

Reference yield:

N-(benzyloxycarbonyl)-L-serine (1145-80-8) → (S)-methyl 2-((S)-3-(benzyloxy)-2-(benzyloxycarbonylamino)propanamido)-3-hydroxypropanoate (75893-22-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) 57percent NaH in Bayol / 1) DMF, 0 deg C, 15 min 2) DMF, 0 deg C, 4 h

2: 1) ethyl chloroformate, Et₃N 2) Et₃N / 1) THF, -10 deg C, 10 min 2) DMF, THF, 0 deg C, 3 h

With chloroformic acid ethyl ester; sodium hydride; triethylamine;

DOI:10.1248/cpb.28.2699

Reference yield:

benzyl bromide (100-39-0) → (S)-methyl 2-((S)-3-(benzyloxy)-2-(benzyloxycarbonylamino)propanamido)-3-hydroxypropanoate (75893-22-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) 57percent NaH in Bayol / 1) DMF, 0 deg C, 15 min 2) DMF, 0 deg C, 4 h

2: 1) ethyl chloroformate, Et₃N 2) Et₃N / 1) THF, -10 deg C, 10 min 2) DMF, THF, 0 deg C, 3 h

With chloroformic acid ethyl ester; sodium hydride; triethylamine;

DOI:10.1248/cpb.28.2699

upstream raw materials:

Z-Ser(Bzl)-OH

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride

N-(benzyloxycarbonyl)-L-serine

benzyl bromide

Downstream raw materials:

cyclo(-L-Ser-L-Ser-)

Z-Ser(Bzl)-Ser-NHNH₂

Z-Ser(OBz)-Gly(SEt)-OMe

Z-Ser(Bzl)-Ser-Ser-Lys(Boc)-NHNH₂