(S)-3-tert-Butoxycarbonylamino-4-isopropoxycarbonyloxy-4-oxo-butyric acid benzyl ester

Base Information

• Chemical Name: (S)-3-tert-Butoxycarbonylamino-4-isopropoxycarbonyloxy-4-oxo-butyric acid benzyl ester
• CAS No.: 118517-08-1
• Molecular Formula: C₂₀H₂₇NO₈
• Molecular Weight: 409.436
• Mol file: 118517-08-1.mol

Synonyms:(S)-3-tert-Butoxycarbonylamino-4-isopropoxycarbonyloxy-4-oxo-butyric acid benzyl ester

Chemical Property of (S)-3-tert-Butoxycarbonylamino-4-isopropoxycarbonyloxy-4-oxo-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-tert-Butoxycarbonylamino-4-isopropoxycarbonyloxy-4-oxo-butyric acid benzyl ester

There total 3 articles about (S)-3-tert-Butoxycarbonylamino-4-isopropoxycarbonyloxy-4-oxo-butyric 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:

BOC-L-aspartic acid 4-benzyl ester (7536-58-5,98482-77-0) + isopropyl chloroformate (108-23-6) → (S)-3-tert-Butoxycarbonylamino-4-isopropoxycarbonyloxy-4-oxo-butyric acid benzyl ester (118517-08-1)

Guidance literature:

With N-methylcyclohexylamine; In dichloromethane; toluene; at 0 ℃; for 0.0333333h;

DOI:10.1021/jm9801096

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-3-tert-Butoxycarbonylamino-4-isopropoxycarbonyloxy-4-oxo-butyric acid benzyl ester (118517-08-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / 1,4-dioxane; water / 0 - 20 °C

2: triethylamine / tetrahydrofuran / 0 °C

With triethylamine; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1016/j.bmcl.2011.01.132

Reference yield:

(S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid (2177-63-1,25248-99-1) → (S)-3-tert-Butoxycarbonylamino-4-isopropoxycarbonyloxy-4-oxo-butyric acid benzyl ester (118517-08-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / 1,4-dioxane; water / 0 - 20 °C

2: triethylamine / tetrahydrofuran / 0 °C

With triethylamine; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1016/j.bmcl.2011.01.132

upstream raw materials:

BOC-L-aspartic acid 4-benzyl ester

isopropyl chloroformate

di-tert-butyl dicarbonate

(S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid

Downstream raw materials:

Boc-Asp(OBzl)-Val-OBzl

(S)-3-tert-Butoxycarbonylamino-N-((S)-1-carbamoyl-2-cyclohexyl-ethyl)-succinamic acid benzyl ester

benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester