(2S,6R)-6-Amino-3,3-dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,6R)-6-Amino-3,3-dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester
• CAS No.: 86062-80-8
• Molecular Formula: C₂₃H₂₅N₃O₄S
• Molecular Weight: 439.535

Synonyms:(2S,6R)-6-Amino-3,3-dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Chemical Property of (2S,6R)-6-Amino-3,3-dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (2S,6R)-6-Amino-3,3-dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

There total 2 articles about (2S,6R)-6-Amino-3,3-dimethyl-7-oxo-6-phenylacetylamino-4-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: 47.0%

(2S,6S)-6-Methanesulfinyl-3,3-dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (86062-79-5,98392-99-5,98393-00-1) → (2S,6R)-6-Amino-3,3-dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (86062-80-8)

Guidance literature:

With ammonia; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(00)98846-4

Reference yield:

benzyl 6α-methylthio-6β-phenylacetamidopenicillanate (56915-14-1) → (2S,6R)-6-Amino-3,3-dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (86062-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0 °C

2: 47 percent / ammonia / CH₂Cl₂ / 0 °C

With ammonia; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/S0040-4039(00)98846-4

Reference yield: 70.0%

(2S,6R)-6-Amino-3,3-dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (86062-80-8) → 6α-formamido penicillin (86062-81-9)

Guidance literature:

With formyl acetic anhydride; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)98846-4

upstream raw materials:

(2S,6S)-6-Methanesulfinyl-3,3-dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

benzyl 6α-methylthio-6β-phenylacetamidopenicillanate

Downstream raw materials:

6α-formamido penicillin

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