(2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Base Information

• Chemical Name: (2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
• CAS No.: 62263-72-3
• Molecular Formula: C₁₅H₁₇NO₃S
• Molecular Weight: 291.371

Synonyms:(2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Chemical Property of (2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of (2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

There total 17 articles about (2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 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: 97.0%

Benzyl 6α-bromopenicillanate (62263-89-2) → (2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (62263-72-3)

Guidance literature:

With tri-n-butyl-tin hydride; In benzene; for 15h; Heating;

DOI:10.1016/S0040-4020(00)00486-5

Reference yield: 91.0%

(2R,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (124831-33-0) → (2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (62263-72-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 8h;

DOI:10.1021/jo00304a024

Reference yield: 81.0%

benzyl 6,6-dibromopenicillanate (35564-99-9) → (2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (62263-72-3)

Guidance literature:

With tri-n-butyl-tin hydride; In benzene; for 24h; Heating;

DOI:10.1016/S0040-4020(00)00486-5

upstream raw materials:

Benzyl 6α-bromopenicillanate

(2R,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

benzyl 6,6-dibromopenicillanate

benzyl (2S)-2-[(4S)-4-chloro-2-oxazetidin-1-yl]-2-(1-chlorothio-1-methylethyl)-acetate

Downstream raw materials:

(2S,5R)-7-[1-Methoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

(2S,5R)-7-[1-Methoxycarbonyl-meth-(E)-ylidene]-3,3-dimethyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

3-Methyl-2-((R)-2-oxo-4-phenylacetylsulfanyl-azetidin-1-yl)-but-2-enoic acid benzyl ester

(2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 4,4-Dioxide

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