(2S,5R,6R)-3-Methylene-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: (2S,5R,6R)-3-Methylene-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester
• CAS No.: 139391-03-0
• Molecular Formula: C₂₃H₂₂N₂O₆S
• Molecular Weight: 454.503

Synonyms:(2S,5R,6R)-3-Methylene-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

Chemical Property of (2S,5R,6R)-3-Methylene-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (2S,5R,6R)-3-Methylene-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

There total 4 articles about (2S,5R,6R)-3-Methylene-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl 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: 84.0%

diphenylmethyl (3R,5R,6R)-2-methylene-6-(phenylacetamido)penam-3-carboxylate (139371-97-4) → (2S,5R,6R)-3-Methylene-4,7-dioxo-6-phenylacetylamino-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester (139391-03-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 5 ℃; for 0.5h;

DOI:10.1016/0040-4039(91)80130-X

Reference yield:

(R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-3-enoic acid benzhydryl ester (119944-09-1) → (2S,5R,6R)-3-Methylene-4,7-dioxo-6-phenylacetylamino-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester (139391-03-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / O₃ / CH₂Cl₂; methanol / -78 °C

2: 76 percent / Et₃N / tetrahydrofuran / 1 h / -40 °C

3: 1) Et₃N, 2) 60percent HClO₄ / 1) DMF, -20 deg C, 0.2 h, 2) -20 deg C

4: 84 percent / mCPBA / CH₂Cl₂ / 0.5 h / 5 °C

With perchloric acid; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/0040-4039(91)80130-X

Reference yield:

(E)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-hydroxy-but-2-enoic acid benzhydryl ester (133696-58-9) → (2S,5R,6R)-3-Methylene-4,7-dioxo-6-phenylacetylamino-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester (139391-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / Et₃N / tetrahydrofuran / 1 h / -40 °C

2: 1) Et₃N, 2) 60percent HClO₄ / 1) DMF, -20 deg C, 0.2 h, 2) -20 deg C

3: 84 percent / mCPBA / CH₂Cl₂ / 0.5 h / 5 °C

With perchloric acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(91)80130-X

upstream raw materials:

diphenylmethyl (3R,5R,6R)-2-methylene-6-(phenylacetamido)penam-3-carboxylate

(R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-3-enoic acid benzhydryl ester

(E)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-hydroxy-but-2-enoic acid benzhydryl ester

(E)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-trifluoromethanesulfonyloxy-but-2-enoic acid benzhydryl ester

Downstream raw materials:

(2S,3R,5R,6R)-3-Allylsulfanylmethyl-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

(2S,3R,5R,6R)-3-(2-Methoxycarbonyl-ethylsulfanylmethyl)-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

(2S,3R,5R,6R)-3-(2-Acetylamino-2-methoxycarbonyl-ethylsulfanylmethyl)-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

(2S,3R,5R,6R)-3-(2-Hydroxy-ethylsulfanylmethyl)-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

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