(2S,5R,6R)-6-Hydroxymethyl-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,6R)-6-Hydroxymethyl-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 81324-22-3
• Molecular Formula: C₂₂H₂₃NO₆S
• Molecular Weight: 429.494

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

Chemical Property:

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

There total 8 articles about (2S,5R,6R)-6-Hydroxymethyl-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: 85.0%

(2S,5R)-6-Bromo-6-hydroxymethyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (229309-40-4) → (2S,5R,6R)-6-Hydroxymethyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (81324-22-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile);

DOI:10.1016/S0960-894X(99)00106-7

Reference yield: 20.0%

(2S,5R)-6-Bromo-6-hydroxymethyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (229309-40-4) → (2S,5R,6R)-6-Hydroxymethyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (81324-22-3) + (2S,5R,6S)-6-Hydroxymethyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (81324-26-7)

Guidance literature:

With tributylphosphine; In methanol;

DOI:10.1016/S0960-894X(99)00106-7

Reference yield:

diphenylmethyl 6,6-dibromopenicillanate (75527-84-3) → (2S,5R,6R)-6-Hydroxymethyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (81324-22-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: t-BuMgBr / -78 °C

1.2: 36 percent / -78 - 20 °C

2.1: 89 percent / nBu₃SnH; AIBN / CH₂Cl₂

3.1: KMnO₄; AcOH / CH₂Cl₂

With potassium permanganate; 2,2'-azobis(isobutyronitrile); tert-butylmagnesium bromide; tri-n-butyl-tin hydride; acetic acid; In dichloromethane;

DOI:10.1016/j.bmcl.2003.12.037

upstream raw materials:

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

diphenylmethyl 6β-(hydroxymethyl)penicillanate

diphenylmethyl 6,6-dibromopenicillanate

diazodiphenylmethane

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