(2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-methanesulfonyloxy pyrrolodine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-methanesulfonyloxy pyrrolodine-2-carboxylic acid methyl ester
• CAS No.: 303188-62-7
• Molecular Formula: C₂₀H₂₇NO₈S
• Molecular Weight: 441.502
• Mol file: 303188-62-7.mol

Synonyms:(2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-methanesulfonyloxy pyrrolodine-2-carboxylic acid methyl ester

Chemical Property of (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-methanesulfonyloxy pyrrolodine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-methanesulfonyloxy pyrrolodine-2-carboxylic acid methyl ester

There total 2 articles about (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-methanesulfonyloxy pyrrolodine-2-carboxylic 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:

(2S,3R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-oxopyrrolidine-2-carboxylic acid methyl ester (169774-61-2) → (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-methanesulfonyloxy pyrrolodine-2-carboxylic acid methyl ester (303188-62-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / methanol / 1.5 h

2: 0.556 g / Et₃N / CH₂Cl₂ / 16 h

With sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(01)00770-0

Reference yield:

methanesulfonyl chloride (124-63-0) + (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (303188-61-6) → (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-methanesulfonyloxy pyrrolodine-2-carboxylic acid methyl ester (303188-62-7)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1016/S0960-894X(00)00352-8

Reference yield: 55.0%

sodium salt of 1-methylimidazole-2-thiolate (50476-76-1) + (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-methanesulfonyloxy pyrrolodine-2-carboxylic acid methyl ester (303188-62-7) → (2S,3S,4S)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-(1-methyl-1H-imidazol-2-sulfanyl)pyrolidine-2-carboxylic acid methyl ester (303188-52-5)

Guidance literature:

In dimethyl sulfoxide; at 90 ℃;

DOI:10.1016/S0960-894X(00)00352-8

upstream raw materials:

methanesulfonyl chloride

(2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester

(2S,3R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-oxopyrrolidine-2-carboxylic acid methyl ester

Downstream raw materials:

(2S,3S,4S)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-phenylsulfanylpyrolidine-2-carboxylic acid methyl ester

(2S,3S,4S)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-[(2-methoxyphenyl)sulfanyl]pyrolidine-2-carboxylic acid methyl ester

(2S,3S,4S)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-(1-methyl-1H-imidazol-2-sulfanyl)pyrolidine-2-carboxylic acid methyl ester