(2RS,3SR,5SR,6RS)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-(2-methylsulphonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

Base Information

• Chemical Name: (2RS,3SR,5SR,6RS)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-(2-methylsulphonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate
• CAS No.: 77058-10-7
• Molecular Formula: C₂₁H₂₇N₃O₉S₂
• Molecular Weight: 529.592
• Mol file: 77058-10-7.mol

Synonyms:

Chemical Property of (2RS,3SR,5SR,6RS)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-(2-methylsulphonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2RS,3SR,5SR,6RS)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-(2-methylsulphonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

There total 1 articles about (2RS,3SR,5SR,6RS)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-(2-methylsulphonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate 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:

2-(acetylamino)ethanethiol (1190-73-4) + (5RS,6SR)-p-nitrobenzyl 6-formylmethyl-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (75440-26-5,77003-45-3) + methanesulfonyl chloride (124-63-0) → (2RS,3RS,5RS,6SR)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-(2-methylsulphonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate + (2RS,3RS,5SR,6RS)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-(2-methylsulphonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate + (2RS,3SR,5SR,6RS)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-(2-methylsulphonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (77003-47-5,77058-10-7,77058-11-8)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1039/c39800001084

Reference yield: 74.0%

(2RS,3SR,5SR,6RS)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-(2-methylsulphonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (77003-47-5,77058-10-7,77058-11-8) → (2RS,3SR,5SR,6RS)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-ethyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (77003-41-9,77058-04-9,77058-05-0,77058-12-9,79056-48-7,79056-57-8,121522-96-1,121523-78-2)

Guidance literature:

With sodium cyanoborohydride; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 95 ℃; for 4h;

DOI:10.1039/c39800001084

Reference yield:

(2S,5R,6S)-3-(2-Acetylamino-ethylsulfanyl)-6-(2-methanesulfonyloxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester (77003-47-5,77058-10-7,77058-11-8) → (2RS,3RS,5SR,6RS)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-ethyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (77003-41-9,77058-04-9,77058-05-0,77058-12-9,79056-48-7,79056-57-8,121522-96-1,121523-78-2) + (2RS,3SR,5SR,6RS)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-ethyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (77003-41-9,77058-04-9,77058-05-0,77058-12-9,79056-48-7,79056-57-8,121522-96-1,121523-78-2)

Guidance literature:

With sodium cyanoborohydride; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 95 ℃; for 4.5h; Yield given. Yields of byproduct given;

upstream raw materials:

2-(acetylamino)ethanethiol

(5RS,6SR)-p-nitrobenzyl 6-formylmethyl-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

methanesulfonyl chloride

Downstream raw materials:

(2RS,3RS,5SR,6RS)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-ethyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

(2RS,3SR,5SR,6RS)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-ethyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate