(2S,5R)-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-, DIPHENYLMETHYL ESTER, 4-OXIDE

Base Information

Chemical Name:(2S,5R)-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-, DIPHENYLMETHYL ESTER, 4-OXIDE
CAS No.:76911-24-5
Molecular Formula:C21H21NO4S
Molecular Weight:383.466
Hs Code.:
Mol file:76911-24-5.mol

Synonyms:(2S,5R)-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-, DIPHENYLMETHYL ESTER, 4-OXIDE

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,5R)-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-, DIPHENYLMETHYL ESTER, 4-OXIDE

Chemical Property:

PSA：89.13000
LogP:3.47190

Purity/Quality:: 95%+ or 98%+ ^*data from raw suppliers

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Technology Process of (2S,5R)-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-, DIPHENYLMETHYL ESTER, 4-OXIDE

There total 2 articles about (2S,5R)-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-, DIPHENYLMETHYL ESTER, 4-OXIDE 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:

: 81324-43-8
(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

: 76911-24-5
(2S,5R)-3,3-Dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 2 steps

1: samarium(II) iodide, HMPA / tetrahydrofuran / 0.5 h

2: samarium(II) iodide, HMPA / tetrahydrofuran / 0.5 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; In tetrahydrofuran;

Reference yield:

: 99651-36-2
benzhydryl 6α-bromopenicillanate S,S-dioxide

: 76911-24-5
(2S,5R)-3,3-Dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; In tetrahydrofuran; for 0.5h; Yield given;

Reference yield: 52.0%

: 4206-67-1
iodo(trimethylsilyl)methane

: 76911-24-5
(2S,5R)-3,3-Dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

: benzhydryl 2-[4(R)-methylsulfonyl-2-oxoazetidinyl-1]-2-(isopropyliden)acetate

Guidance literature:: (2S,5R)-3,3-Dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.0833333h;

iodo(trimethylsilyl)methane; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1023/B:COHC.0000040782.42204.4f