(2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester
• CAS No.: 76946-53-7
• Molecular Formula: C₁₅H₁₇NO₄S
• Molecular Weight: 307.37

Synonyms:(2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Chemical Property of (2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

There total 7 articles about (2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic 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: 68.0%

(2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (62263-72-3) → (2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (76946-53-7) + benzyl (+)-(2S,4S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 0 ℃; for 1.41667h;

DOI:10.1016/S0040-4020(00)00486-5

Reference yield:

benzyl bromide (100-39-0) → (2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (76946-53-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / Et₃N / dimethylformamide / 15 h / 20 °C

2: 97 percent / n-Bu₃SnH / benzene / 15 h / Heating

3: m-chloroperbenzoic acid / CHCl₃ / 1.42 h / 0 °C

With tri-n-butyl-tin hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In chloroform; N,N-dimethyl-formamide; benzene; 1: Esterification / 2: reductive dehalogenation / 3: Oxidation;

DOI:10.1016/S0040-4020(00)00486-5

Reference yield:

6-bromopenicillanic acid (24138-28-1) → (2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (76946-53-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / Et₃N / dimethylformamide / 15 h / 20 °C

2: 97 percent / n-Bu₃SnH / benzene / 15 h / Heating

3: m-chloroperbenzoic acid / CHCl₃ / 1.42 h / 0 °C

With tri-n-butyl-tin hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In chloroform; N,N-dimethyl-formamide; benzene; 1: Esterification / 2: reductive dehalogenation / 3: Oxidation;

DOI:10.1016/S0040-4020(00)00486-5

upstream raw materials:

(2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

6-bromopenicillanic acid

Benzyl 6α-bromopenicillanate

benzyl 6,6-dibromopenicillanate

Downstream raw materials:

(R)-2-((S)-2-Acetoxy-4-oxo-azetidin-1-yl)-3-methyl-but-3-enoic acid benzyl ester

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