(2S,5R,6S)-6-Acetylsulfanyl-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-Acetylsulfanyl-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 683751-13-5
• Molecular Formula: C₂₃H₂₃NO₆S₂
• Molecular Weight: 473.571
• Mol file: 683751-13-5.mol

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (2S,5R,6S)-6-Acetylsulfanyl-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: 60.0%

(2S,5R,6S)-6-Acetylsulfanyl-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (683751-07-7) → (2S,5R,6S)-6-Acetylsulfanyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (683751-13-5)

Guidance literature:

With potassium permanganate; acetic acid; at 20 ℃; for 15h;

DOI:10.1016/j.bmcl.2003.12.037

Reference yield:

6-Aminopenicillanic Acid (551-16-6) → (2S,5R,6S)-6-Acetylsulfanyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (683751-13-5)

Guidance literature:

Multi-step reaction with 4 steps

1: iPrONO; TFA

2: 40 percent / BF₃*OEt₂ / 0.25 h / 20 °C

3: 60 percent / KMnO₄; AcOH / 15 h / 20 °C

With potassium permanganate; i-propyl nitrite; boron trifluoride diethyl etherate; acetic acid; trifluoroacetic acid;

DOI:10.1016/j.bmcl.2003.12.037

Reference yield:

diphenylmethyl 6-diazopenicillanate (65293-13-2) → (2S,5R,6S)-6-Acetylsulfanyl-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (683751-13-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / BF₃*OEt₂ / 0.25 h / 20 °C

2: 60 percent / KMnO₄; AcOH / 15 h / 20 °C

With potassium permanganate; boron trifluoride diethyl etherate; acetic acid;

DOI:10.1016/j.bmcl.2003.12.037

upstream raw materials:

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

6-Aminopenicillanic Acid

diphenylmethyl 6-diazopenicillanate

diazodiphenylmethane

Downstream raw materials:

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