(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

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 bis-(4-nitro-benzyl) ester
• CAS No.: 111924-25-5
• Molecular Formula: C₃₀H₂₆N₄O₁₂S
• Molecular Weight: 666.622

Synonyms:

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 bis-(4-nitro-benzyl) ester

Chemical Property:

Purity/Quality:

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Useful:

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 bis-(4-nitro-benzyl) ester

There total 3 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 bis-(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: 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

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 bis-(4-nitro-benzyl) ester (111924-25-5)

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: 88 percent

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

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,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:

Multi-step reaction with 2 steps

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

2: 88 percent

With sodium chlorite; recorcinol; In tetrahydrofuran; water;

DOI:10.1039/c39870000081

upstream raw materials:

(4-nitrophenyl)diazomethane

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

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