(2S,5R,6S)-6-[(E)-3-(Methoxy-methyl-carbamoyl)-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-[(E)-3-(Methoxy-methyl-carbamoyl)-allyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 345203-80-7
• Molecular Formula: C₂₇H₃₀N₂O₇S
• Molecular Weight: 526.61

Synonyms:

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

Chemical Property:

Purity/Quality:

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

There total 4 articles about (2S,5R,6S)-6-[(E)-3-(Methoxy-methyl-carbamoyl)-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:

benzhydryl 6α-bromopenicillanate S,S-dioxide (99651-36-2) → (2S,5R,6S)-6-[(E)-3-(Methoxy-methyl-carbamoyl)-allyl]-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (345203-80-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 79 percent / AIBN

2.1: O₃ / methanol

2.2: 69 percent / Me₂S / methanol

3.1: benzene

With 2,2'-azobis(isobutyronitrile); ozone; In methanol; benzene; 3.1: Wittig reaction;

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-[(E)-3-(Methoxy-methyl-carbamoyl)-allyl]-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (345203-80-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 86 percent / EtMgBr / -78 °C

2.1: 79 percent / AIBN

3.1: O₃ / methanol

3.2: 69 percent / Me₂S / methanol

4.1: benzene

With 2,2'-azobis(isobutyronitrile); ethylmagnesium bromide; ozone; In methanol; benzene; 4.1: Wittig reaction;

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

Reference yield:

(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)-6-[(E)-3-(Methoxy-methyl-carbamoyl)-allyl]-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (345203-80-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: O₃ / methanol

1.2: 69 percent / Me₂S / methanol

2.1: benzene

With ozone; In methanol; benzene; 2.1: Wittig reaction;

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

upstream raw materials:

N-methoxy-N-methyl-2-(triphenylphosphoranylidene)acetamide

(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

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

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