(6R,7S)-3-Acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-tert-butoxycarbonyl-benzyl ester

Base Information

• Chemical Name: (6R,7S)-3-Acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-tert-butoxycarbonyl-benzyl ester
• CAS No.: 128472-60-6
• Molecular Formula: C₂₃H₂₇NO₈S
• Molecular Weight: 477.535
• Mol file: 128472-60-6.mol

Synonyms:

Chemical Property of (6R,7S)-3-Acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-tert-butoxycarbonyl-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,7S)-3-Acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-tert-butoxycarbonyl-benzyl ester

There total 4 articles about (6R,7S)-3-Acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-tert-butoxycarbonyl-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:

4-hydroxymethylbenzoic acid tert-butyl ester (143726-85-6) → (6R,7S)-3-Acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-tert-butoxycarbonyl-benzyl ester (128472-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1: cuprous chloride / 72 h / Ambient temperature

2: tetrahydrofuran / 18 h / Ambient temperature

With copper(l) chloride; In tetrahydrofuran;

DOI:10.1021/jm00171a029

Reference yield:

t-butyl 3-acetoxymethyl-7α-methoxy-3-cephem-4-carboxylate (95570-83-5) → (6R,7S)-3-Acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-tert-butoxycarbonyl-benzyl ester (128472-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid (TFA), anisole / 0.5 h / 0 °C

2: tetrahydrofuran / 18 h / Ambient temperature

With methoxybenzene; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/jm00171a029

Reference yield:

7-Aminocephalosporanic acid (957-68-6) → (6R,7S)-3-Acetoxymethyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-tert-butoxycarbonyl-benzyl ester (128472-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1: isoamyl nitrite, 7 N perchloric acid / 0.5 h / 50 - 60 °C

2: tetrahydrofuran / 18 h / Ambient temperature

With perchloric acid; isopentyl nitrite; In tetrahydrofuran;

DOI:10.1021/jm00171a029

upstream raw materials:

4-(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

4-hydroxymethylbenzoic acid tert-butyl ester

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