(5S,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-hydroxy-3-oxo-heptanoic acid tert-butyl ester

Base Information

• Chemical Name: (5S,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-hydroxy-3-oxo-heptanoic acid tert-butyl ester
• CAS No.: 910252-33-4
• Molecular Formula: C₂₆H₃₃NO₇
• Molecular Weight: 471.551
• Mol file: 910252-33-4.mol

Synonyms:(5S,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-hydroxy-3-oxo-heptanoic acid tert-butyl ester

Chemical Property of (5S,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-hydroxy-3-oxo-heptanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-hydroxy-3-oxo-heptanoic acid tert-butyl ester

There total 4 articles about (5S,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-hydroxy-3-oxo-heptanoic acid tert-butyl 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: 75.0%

acetic acid tert-butyl ester (540-88-5) + (3S,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl ester (910252-32-3) → (5S,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-hydroxy-3-oxo-heptanoic acid tert-butyl ester (910252-33-4)

Guidance literature:

acetic acid tert-butyl ester; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

(3S,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl ester; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 1.5h;

DOI:10.1055/s-2006-941602

Reference yield:

Z-Ser(Bzl)-OH (20806-43-3) → (5S,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-hydroxy-3-oxo-heptanoic acid tert-butyl ester (910252-33-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: MgCl₂

2.1: NaBH₄ / diethyl ether

3.1: n-BuLi; i-Pr₂NH / hexane; tetrahydrofuran / 1 h / -78 °C

3.2: 75 percent / hexane; tetrahydrofuran / 1.5 h / 0 - 20 °C

With sodium tetrahydroborate; n-butyllithium; diisopropylamine; magnesium chloride; In tetrahydrofuran; diethyl ether; hexane; 4.2: Heathcock-Claisen condensation;

DOI:10.1055/s-2006-941602

Reference yield:

((S)-1-Benzyloxymethyl-2-imidazol-1-yl-2-oxo-ethyl)-carbamic acid benzyl ester → (5S,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-hydroxy-3-oxo-heptanoic acid tert-butyl ester (910252-33-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: MgCl₂

2.1: NaBH₄ / diethyl ether

3.1: n-BuLi; i-Pr₂NH / hexane; tetrahydrofuran / 1 h / -78 °C

3.2: 75 percent / hexane; tetrahydrofuran / 1.5 h / 0 - 20 °C

With sodium tetrahydroborate; n-butyllithium; diisopropylamine; magnesium chloride; In tetrahydrofuran; diethyl ether; hexane; 3.2: Heathcock-Claisen condensation;

DOI:10.1055/s-2006-941602

upstream raw materials:

acetic acid tert-butyl ester

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

Z-Ser(Bzl)-OH

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

Downstream raw materials:

7-benzyloxy-6-benzyloxycarbonylamino-3,5-dihydroxy-heptanoic acid tert-butyl ester

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