(2S,5R,6S)-6-Allyl-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,5R,6S)-6-Allyl-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 176220-71-6
• Molecular Formula: C₂₄H₂₅NO₅S
• Molecular Weight: 439.532

Synonyms:(2S,5R,6S)-6-Allyl-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property of (2S,5R,6S)-6-Allyl-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

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Technology Process of (2S,5R,6S)-6-Allyl-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

There total 2 articles about (2S,5R,6S)-6-Allyl-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl 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: 79.0%

allyltributylstanane (24850-33-7) + benzhydryl 6α-bromopenicillanate S,S-dioxide (99651-36-2) → (2S,5R,6S)-6-Allyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (176220-71-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile);

DOI:10.1016/S0960-894X(01)00148-2

Reference yield:

(2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester (81324-43-8) → (2S,5R,6S)-6-Allyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (176220-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / EtMgBr / -78 °C

2: 79 percent / AIBN

With 2,2'-azobis(isobutyronitrile); ethylmagnesium bromide;

DOI:10.1016/S0960-894X(01)00148-2

Reference yield: 69.0%

(2S,5R,6S)-6-Allyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (176220-71-6) → (2S,5R,6S)-3,3-Dimethyl-4,4,7-trioxo-6-(2-oxo-ethyl)-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (345203-77-2)

Guidance literature:

(2S,5R,6S)-6-Allyl-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester; With ozone; In methanol;

With dimethylsulfide; In methanol;

DOI:10.1016/S0960-894X(01)00148-2

upstream raw materials:

allyltributylstanane

benzhydryl 6α-bromopenicillanate S,S-dioxide

(2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester

Downstream raw materials:

(2S,5R,6S)-3,3-Dimethyl-4,4,7-trioxo-6-(2-oxo-ethyl)-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,5R,6S)-3,3-Dimethyl-4,4,7-trioxo-6-((E)-4-oxo-but-2-enyl)-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,5R,6S)-3,3-Dimethyl-4,4,7-trioxo-6-((E)-4-oxo-pent-2-enyl)-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,5R,6S)-6-((E)-3-Methoxycarbonyl-allyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

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