methyl (3S,4S)-N-tert-butoxycarbonyl-4-amino-3-hydroxy-5-phenylpentanoate

Base Information

• Chemical Name: methyl (3S,4S)-N-tert-butoxycarbonyl-4-amino-3-hydroxy-5-phenylpentanoate
• CAS No.: 101669-80-1
• Molecular Formula: C₁₇H₂₅NO₅
• Molecular Weight: 323.389
• Mol file: 101669-80-1.mol

Synonyms:methyl (3S,4S)-N-tert-butoxycarbonyl-4-amino-3-hydroxy-5-phenylpentanoate

Chemical Property of methyl (3S,4S)-N-tert-butoxycarbonyl-4-amino-3-hydroxy-5-phenylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl (3S,4S)-N-tert-butoxycarbonyl-4-amino-3-hydroxy-5-phenylpentanoate

There total 8 articles about methyl (3S,4S)-N-tert-butoxycarbonyl-4-amino-3-hydroxy-5-phenylpentanoate 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: 90.0%

(4S,5R)-N-(((tert)-butyloxy)carbonyl)-5-benzyl-4-hydroxy-2-pyrrolidinone (109579-10-4,109579-13-7,144186-19-6) + sodium methylate (124-41-4) → methyl (3S,4S)-N-tert-butoxycarbonyl-4-amino-3-hydroxy-5-phenylpentanoate (101669-80-1)

Guidance literature:

In methanol; Ambient temperature;

Reference yield: 82.0%

methyl (3S,4S)-3-O-formyl-4-(tert-butoxycarbonyl)amino-5-phenylpentanoate (1350846-57-9) → methyl (3S,4S)-N-tert-butoxycarbonyl-4-amino-3-hydroxy-5-phenylpentanoate (101669-80-1)

Guidance literature:

With methanol; toluene-4-sulfonic acid; at 20 ℃; for 1h;

DOI:10.1016/j.tetasy.2011.09.021

Reference yield:

methanol (67-56-1) + (3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenyl-pentanoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester (118219-44-6,118246-41-6) → methyl (3S,4S)-N-tert-butoxycarbonyl-4-amino-3-hydroxy-5-phenylpentanoate (101669-80-1)

Guidance literature:

With sodium methylate; In 1,4-dioxane; at 0 ℃; Yield given;

DOI:10.1016/S0040-4039(00)86044-X

upstream raw materials:

methanol

(3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenyl-pentanoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester

(4S,5R)-N-(((tert)-butyloxy)carbonyl)-5-benzyl-4-hydroxy-2-pyrrolidinone

sodium methylate

Downstream raw materials:

(3S,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-phenylpentanoic acid

(4S,5S)-4-Benzyl-5-(2-methanesulfonyloxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4S,5S)-4-benzyl-5-(2-carboxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

(S)-4-benzyl-5-(2-cyanoethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester