3-benzyloxycarbonylamino-4-methanesulfonyloxy-butyric acid tert-butyl ester

Base Information

• Chemical Name: 3-benzyloxycarbonylamino-4-methanesulfonyloxy-butyric acid tert-butyl ester
• CAS No.: 761435-43-2
• Molecular Formula: C₁₇H₂₅NO₇S
• Molecular Weight: 387.454
• Mol file: 761435-43-2.mol

Synonyms:3-benzyloxycarbonylamino-4-methanesulfonyloxy-butyric acid tert-butyl ester

Chemical Property of 3-benzyloxycarbonylamino-4-methanesulfonyloxy-butyric acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-benzyloxycarbonylamino-4-methanesulfonyloxy-butyric acid tert-butyl ester

There total 2 articles about 3-benzyloxycarbonylamino-4-methanesulfonyloxy-butyric 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: 97.0%

methanesulfonyl chloride (124-63-0) + (R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester (146398-01-8) → 3-benzyloxycarbonylamino-4-methanesulfonyloxy-butyric acid tert-butyl ester (761435-43-2)

Guidance literature:

With TEA; In dichloromethane;

DOI:10.1016/j.bmcl.2004.06.049

Reference yield:

(2R)-2-{[(benzyloxy)carbonyl]amino}-4-tert-butoxy-4-oxobutanoic acid (71449-08-6) → 3-benzyloxycarbonylamino-4-methanesulfonyloxy-butyric acid tert-butyl ester (761435-43-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / BH₃ / tetrahydrofuran

2: 97 percent / TEA / CH₂Cl₂

With TEA; borane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2004.06.049

Reference yield: 60.0%

4-sulfanylphenol (637-89-8) + 3-benzyloxycarbonylamino-4-methanesulfonyloxy-butyric acid tert-butyl ester (761435-43-2) → 3-benzyloxycarbonylamino-4-(4-hydroxy-phenylsulfanyl)-butyric acid tert-butyl ester (761435-45-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmcl.2004.06.049

upstream raw materials:

methanesulfonyl chloride

(R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester

(2R)-2-{[(benzyloxy)carbonyl]amino}-4-tert-butoxy-4-oxobutanoic acid

Downstream raw materials:

3-benzyloxycarbonylamino-4-(4-hydroxy-phenylsulfanyl)-butyric acid tert-butyl ester

(2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-3-carboxylic acid tert-butyl ester

(2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-piperidine-3-carboxylic acid tert-butyl ester

(2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-1,3-dicarboxylic acid di-tert-butyl ester