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

Base Information

• Chemical Name: (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 683751-10-2
• Molecular Formula: C₂₄H₂₂Cl₃NO₇S₂
• Molecular Weight: 606.932

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 7 articles about (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-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:

6-Aminopenicillanic Acid (551-16-6) → (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (683751-10-2)

Guidance literature:

Multi-step reaction with 7 steps

1: NaNO₂; aq. HClO₄

2: Et₃N

3: acetonitrile

4: 80 percent / NaOMe / tetrahydrofuran; methanol / 8 h / -78 °C

5: 73 percent / DMAP / 3 h / 0 - 20 °C

6: KMnO₄; AcOH / 15 h / 20 °C

With dmap; potassium permanganate; perchloric acid; sodium methylate; acetic acid; triethylamine; sodium nitrite; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1016/j.bmcl.2003.12.037

Reference yield:

6-α-hydroxypenicillanic acid (15058-64-7) → (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (683751-10-2)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N

2: acetonitrile

3: 80 percent / NaOMe / tetrahydrofuran; methanol / 8 h / -78 °C

4: 73 percent / DMAP / 3 h / 0 - 20 °C

5: KMnO₄; AcOH / 15 h / 20 °C

With dmap; potassium permanganate; sodium methylate; acetic acid; triethylamine; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1016/j.bmcl.2003.12.037

Reference yield:

(2S,5R,6R)-6-Acetylsulfanyl-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (75722-86-0) → (2S,5R,6R)-3,3-Dimethyl-4,4,7-trioxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (683751-10-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / NaOMe / tetrahydrofuran; methanol / 8 h / -78 °C

2: 73 percent / DMAP / 3 h / 0 - 20 °C

3: KMnO₄; AcOH / 15 h / 20 °C

With dmap; potassium permanganate; sodium methylate; acetic acid; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmcl.2003.12.037

upstream raw materials:

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

6-Aminopenicillanic Acid

6-α-hydroxypenicillanic acid

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

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

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