(2S,5R,6S)-6-Mercaptomethyl-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-Mercaptomethyl-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 615551-66-1
• Molecular Formula: C₂₂H₂₃NO₅S₂
• Molecular Weight: 445.56

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

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Technology Process of (2S,5R,6S)-6-Mercaptomethyl-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,6S)-6-Mercaptomethyl-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: 54.0%

(2S,5R,6S)-3,3-Dimethyl-4,4,7-trioxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanylmethyl)-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (615551-65-0) → (2S,5R,6S)-6-Mercaptomethyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (615551-66-1)

Guidance literature:

With copper; acetic acid; zinc; In tetrahydrofuran; methanol; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2003.12.037

Reference yield:

diphenylmethyl 6,6-dibromopenicillanate (75527-84-3) → (2S,5R,6S)-6-Mercaptomethyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (615551-66-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: t-BuMgBr / -78 °C

1.2: 36 percent / -78 - 20 °C

2.1: 89 percent / nBu₃SnH; AIBN / CH₂Cl₂

3.1: 74 percent / DMAP / CHCl₃ / 3 h

4.1: 77 percent / acetonitrile / 15 h / 20 °C

5.1: 85 percent / NaOMe / tetrahydrofuran; methanol / -78 - -40 °C

6.1: 83 percent / DMAP / CH₂Cl₂ / 3 h / 0 - 20 °C

7.1: KMnO₄; AcOH / CH₂Cl₂ / 14 h / 20 °C

8.1: 54 percent / Zn-Cu; AcOH / tetrahydrofuran; methanol / 1 h / 20 °C

With dmap; potassium permanganate; 2,2'-azobis(isobutyronitrile); tert-butylmagnesium bromide; tri-n-butyl-tin hydride; sodium methylate; copper; acetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetonitrile;

DOI:10.1016/j.bmcl.2003.12.037

Reference yield:

6,6-dibromopenicillanic acid (24158-88-1) → (2S,5R,6S)-6-Mercaptomethyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (615551-66-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 90 percent / acetone / 14 h / 20 °C

2.1: t-BuMgBr / -78 °C

2.2: 36 percent / -78 - 20 °C

3.1: 89 percent / nBu₃SnH; AIBN / CH₂Cl₂

4.1: 74 percent / DMAP / CHCl₃ / 3 h

5.1: 77 percent / acetonitrile / 15 h / 20 °C

6.1: 85 percent / NaOMe / tetrahydrofuran; methanol / -78 - -40 °C

7.1: 83 percent / DMAP / CH₂Cl₂ / 3 h / 0 - 20 °C

8.1: KMnO₄; AcOH / CH₂Cl₂ / 14 h / 20 °C

9.1: 54 percent / Zn-Cu; AcOH / tetrahydrofuran; methanol / 1 h / 20 °C

With dmap; potassium permanganate; 2,2'-azobis(isobutyronitrile); tert-butylmagnesium bromide; tri-n-butyl-tin hydride; sodium methylate; copper; acetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetone; acetonitrile;

DOI:10.1016/j.bmcl.2003.12.037

upstream raw materials:

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

diphenylmethyl 6,6-dibromopenicillanate

6,6-dibromopenicillanic acid

diphenylmethyl 6β-(hydroxymethyl)penicillanate

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