(2S,3R,5R,6R)-3-Methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-(4-nitro-benzyl) ester

Base Information

• Chemical Name: (2S,3R,5R,6R)-3-Methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-(4-nitro-benzyl) ester
• CAS No.: 111924-28-8
• Molecular Formula: C₂₃H₂₁N₃O₉S
• Molecular Weight: 515.5
• Mol file: 111924-28-8.mol

Synonyms:(2S,3R,5R,6R)-3-Methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-(4-nitro-benzyl) ester

Chemical Property of (2S,3R,5R,6R)-3-Methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-(4-nitro-benzyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5R,6R)-3-Methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-(4-nitro-benzyl) ester

There total 3 articles about (2S,3R,5R,6R)-3-Methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-(4-nitro-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: 66.0%

(2S,3R,4S,5R,6R)-3-Methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-(4-nitro-benzyl) ester (111924-24-4) → (2S,3R,5R,6R)-3-Methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-(4-nitro-benzyl) ester (111924-28-8)

Guidance literature:

With phosphorus tribromide; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1039/c39870000081

Reference yield:

10-hydroxy-1β-oxo-6β-(2-phenoxy-acetylamino)-1λ4-penicillanic acid 4-nitro-benzyl ester (70850-45-2) → (2S,3R,5R,6R)-3-Methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-(4-nitro-benzyl) ester (111924-28-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / dimethyl sulphoxide / acetic anhydride / 20 °C

2: 90 percent / sodium chlorite, resorcinol / tetrahydrofuran; H₂O; various solvent(s) / pH 3.5

3: 66 percent / PBr₃ / dimethylformamide / 0 °C

With sodium chlorite; phosphorus tribromide; dimethyl sulfoxide; recorcinol; In tetrahydrofuran; water; acetic anhydride; N,N-dimethyl-formamide;

DOI:10.1039/c39870000081

Reference yield:

(2S,3R,4S,5R,6R)-3-Formyl-3-methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester (111924-23-3) → (2S,3R,5R,6R)-3-Methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-(4-nitro-benzyl) ester (111924-28-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / sodium chlorite, resorcinol / tetrahydrofuran; H₂O; various solvent(s) / pH 3.5

2: 66 percent / PBr₃ / dimethylformamide / 0 °C

With sodium chlorite; phosphorus tribromide; recorcinol; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1039/c39870000081

upstream raw materials:

(2S,3R,4S,5R,6R)-3-Methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-(4-nitro-benzyl) ester

10-hydroxy-1β-oxo-6β-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid 4-nitro-benzyl ester

(2S,3R,4S,5R,6R)-3-Formyl-3-methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Downstream raw materials:

(2S,3R,5R,6R)-3-Dimethylcarbamoyl-3-methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester