(3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl ester

Base Information

• Chemical Name: (3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl ester
• CAS No.: 752251-09-5
• Molecular Formula: C₂₁H₂₅NO₆
• Molecular Weight: 387.433
• Mol file: 752251-09-5.mol

Synonyms:(3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl ester

Chemical Property of (3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl ester

There total 3 articles about (3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl 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: 48.0%

(4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-oxo-pentanoic acid methyl ester (752251-08-4) → (3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl ester (752251-09-5) + (3S,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl ester (910252-32-3)

Guidance literature:

With sodium tetrahydroborate; In methanol; diethyl ether; at -60 ℃; for 6h;

DOI:10.1002/anie.200453909

Reference yield:

Z-Ser(Bzl)-OH (20806-43-3) → (3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl ester (752251-09-5)

Guidance literature:

Multi-step reaction with 3 steps

1: MgCl₂

2: NaBH₄ / diethyl ether

With sodium tetrahydroborate; magnesium chloride; In diethyl ether;

DOI:10.1055/s-2006-941602

Reference yield:

((S)-1-Benzyloxymethyl-2-imidazol-1-yl-2-oxo-ethyl)-carbamic acid benzyl ester → (3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl ester (752251-09-5)

Guidance literature:

Multi-step reaction with 2 steps

1: MgCl₂

2: NaBH₄ / diethyl ether

With sodium tetrahydroborate; magnesium chloride; In diethyl ether;

DOI:10.1055/s-2006-941602

upstream raw materials:

(4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-oxo-pentanoic acid methyl ester

Z-Ser(Bzl)-OH

Downstream raw materials:

(3R,5R,6S)-6-(2-benzyloxybenzoylamino)-3,5,7-tris-(tert-butyldimethylsilanyloxy)heptanoic acid

(3R,5R,6S)-6-(2-benzyloxy-benzoylamino)-3,5,7-tris-(tert-butyl-dimethyl-silanyloxy)heptanoic acid methyl ester

(3R,5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-3,5-bis(tert-butyl-dimethylsilanyloxy)-heptanoic acid methyl ester

(5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-oxoheptanoic acid methyl ester