(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

Base Information

• Chemical Name: (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
• CAS No.: 111924-24-4
• Molecular Formula: C₂₃H₂₁N₃O₁₀S
• Molecular Weight: 531.5

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 2 articles about (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 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: 90.0%

(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,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)

Guidance literature:

With sodium chlorite; recorcinol; In tetrahydrofuran; water; pH 3.5;

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,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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium chlorite; dimethyl sulfoxide; recorcinol; In tetrahydrofuran; water; acetic anhydride;

DOI:10.1039/c39870000081

Reference yield: 88.0%

(4-nitrophenyl)diazomethane (19479-80-2) + (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,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 bis-(4-nitro-benzyl) ester (111924-25-5)

Guidance literature:

DOI:10.1039/c39870000081

upstream raw materials:

(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

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

Downstream 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 bis-(4-nitro-benzyl) ester

(5R)-3-methyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

4-nitrobenzyl (3R,5R,6R)-2-methylene-6-(phenoxyacetamido)penam-3-carboxylate

(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

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