(2R,5S)-3,3,7-Trioxo-3λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2R,5S)-3,3,7-Trioxo-3λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester
• CAS No.: 88517-50-4
• Molecular Formula: C₁₃H₁₃NO₅S
• Molecular Weight: 295.316

Synonyms:(2R,5S)-3,3,7-Trioxo-3λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Chemical Property of (2R,5S)-3,3,7-Trioxo-3λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (2R,5S)-3,3,7-Trioxo-3λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

There total 4 articles about (2R,5S)-3,3,7-Trioxo-3λ⁶-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: 95.0%

Diazo-(4-oxo-azetidin-2-ylmethanesulfonyl)-acetic acid benzyl ester (88517-49-1) → (2R,5S)-3,3,7-Trioxo-3λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (88517-50-4)

Guidance literature:

With rhodium(II) acetate; In benzene; at 80 ℃;

DOI:10.1016/S0040-4039(00)86241-3

Reference yield:

mercaptoacetic acid benzyl ester (7383-63-3) → (2R,5S)-3,3,7-Trioxo-3λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (88517-50-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / NaH / tetrahydrofuran / from 0 to 20 degC

2: 90 percent / Oxone / methanol; H₂O

3: 83 percent / p-carboxybenzenesulphonyl azide, triethylamine / acetonitrile

4: 95 percent / Rh(OAc)2 / benzene / 80 °C

With rhodium(II) acetate; Oxone; p-carboxybenzenesulfonyl azide; sodium hydride; triethylamine; In tetrahydrofuran; methanol; water; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)86241-3

Reference yield:

(4-Oxo-azetidin-2-ylmethanesulfonyl)-acetic acid benzyl ester → (2R,5S)-3,3,7-Trioxo-3λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (88517-50-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / p-carboxybenzenesulphonyl azide, triethylamine / acetonitrile

2: 95 percent / Rh(OAc)2 / benzene / 80 °C

With rhodium(II) acetate; p-carboxybenzenesulfonyl azide; triethylamine; In acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)86241-3

upstream raw materials:

Diazo-(4-oxo-azetidin-2-ylmethanesulfonyl)-acetic acid benzyl ester

mercaptoacetic acid benzyl ester

[(S)-1-(tert-Butyl-dimethyl-silanyl)-4-oxo-azetidin-2-ylmethylsulfanyl]-acetic acid benzyl ester

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