(6R,7S)-3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 3-carboxy-benzyl ester

Base Information

• Chemical Name: (6R,7S)-3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 3-carboxy-benzyl ester
• CAS No.: 128472-67-3
• Molecular Formula: C₁₉H₁₉NO₁₀S
• Molecular Weight: 453.427

Synonyms:(6R,7S)-3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 3-carboxy-benzyl ester

Chemical Property of (6R,7S)-3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 3-carboxy-benzyl ester

Chemical Property:

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Technology Process of (6R,7S)-3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 3-carboxy-benzyl ester

There total 6 articles about (6R,7S)-3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 3-carboxy-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: 96.0%

(6R,7S)-3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 3-tert-butoxycarbonyl-benzyl ester → (6R,7S)-3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 3-carboxy-benzyl ester (128472-67-3)

Guidance literature:

With methoxybenzene; trifluoroacetic acid; at 0 ℃; for 0.5h;

DOI:10.1021/jm00171a029

Reference yield:

3-hydroxymethyl-benzoic acid tert-butyl ester (215522-96-6) → (6R,7S)-3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 3-carboxy-benzyl ester (128472-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1: cuprous chloride / 72 h / Ambient temperature

2: 2.) 85percent m-chloroperbenzoic acid (m-CPBA) / 1.) THF, RT, 18 h, 2.) CH₂Cl₂, RT, 18 h

3: 96 percent / anisole, trifluoroacetic acid (TFA) / 0.5 h / 0 °C

With methoxybenzene; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; copper(l) chloride;

DOI:10.1021/jm00171a029

Reference yield:

3-(N,N'-Diisopropyl-carbamimidoyloxymethyl)-benzoic acid tert-butyl ester (128473-00-7) → (6R,7S)-3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 3-carboxy-benzyl ester (128472-67-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) 85percent m-chloroperbenzoic acid (m-CPBA) / 1.) THF, RT, 18 h, 2.) CH₂Cl₂, RT, 18 h

2: 96 percent / anisole, trifluoroacetic acid (TFA) / 0.5 h / 0 °C

With methoxybenzene; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid;

DOI:10.1021/jm00171a029

upstream raw materials:

3-hydroxymethyl-benzoic acid tert-butyl ester

3-(N,N'-Diisopropyl-carbamimidoyloxymethyl)-benzoic acid tert-butyl ester

3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

t-butyl 3-acetoxymethyl-7α-methoxy-3-cephem-4-carboxylate

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