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

Base Information

• Chemical Name: (2S,5R,6R)-6-(2-Benzyloxycarbonylamino-ethanesulfonylamino)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester
• CAS No.: 176657-00-4
• Molecular Formula: C₂₀H₂₇N₃O₁₀S₂
• Molecular Weight: 533.58

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

Chemical Property of (2S,5R,6R)-6-(2-Benzyloxycarbonylamino-ethanesulfonylamino)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester

Chemical Property:

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

There total 4 articles about (2S,5R,6R)-6-(2-Benzyloxycarbonylamino-ethanesulfonylamino)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl 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: 72.0%

(2S,5R,6R)-6-(2-Benzyloxycarbonylamino-ethanesulfonylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester (176656-99-8) → (2S,5R,6R)-6-(2-Benzyloxycarbonylamino-ethanesulfonylamino)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester (176657-00-4)

Guidance literature:

With potassium permanganate; acetic acid; at -10 ℃; for 1h;

DOI:10.1016/0040-4020(96)00197-4

Reference yield:

benzyl (2-(chlorosulfonyl)ethyl)carbamate (52530-50-4) → (2S,5R,6R)-6-(2-Benzyloxycarbonylamino-ethanesulfonylamino)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester (176657-00-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 42 percent / Et₃N / CH₂Cl₂ / 0.33 h / 20 °C

2: 72 percent / aq. KMnO₄, aq. AcOH / 1 h / -10 °C

With potassium permanganate; acetic acid; triethylamine; In dichloromethane;

DOI:10.1016/0040-4020(96)00197-4

Reference yield:

N-Benzyloxycarbonyl-taurine sodium salt (136027-16-2) → (2S,5R,6R)-6-(2-Benzyloxycarbonylamino-ethanesulfonylamino)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester (176657-00-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / POCl₃ / tetrahydrothiophene 1,1-dioxide; acetonitrile / 0.67 h / 70 °C

2: 42 percent / Et₃N / CH₂Cl₂ / 0.33 h / 20 °C

3: 72 percent / aq. KMnO₄, aq. AcOH / 1 h / -10 °C

With potassium permanganate; acetic acid; triethylamine; trichlorophosphate; In sulfolane; dichloromethane; acetonitrile;

DOI:10.1016/0040-4020(96)00197-4

upstream raw materials:

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

benzyl (2-(chlorosulfonyl)ethyl)carbamate

N-Benzyloxycarbonyl-taurine sodium salt

benzyl chloroformate

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