4-(tert-butoxycarbonyl)benzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide

Base Information

• Chemical Name: 4-(tert-butoxycarbonyl)benzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide
• CAS No.: 128472-66-2
• Molecular Formula: C₂₃H₂₇NO₁₀S
• Molecular Weight: 509.534
• Mol file: 128472-66-2.mol

Synonyms:4-(tert-butoxycarbonyl)benzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide

Chemical Property of 4-(tert-butoxycarbonyl)benzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(tert-butoxycarbonyl)benzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide

There total 4 articles about 4-(tert-butoxycarbonyl)benzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide 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) → 4-(tert-butoxycarbonyl)benzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide (128472-66-2)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1021/jm00171a029

Reference yield:

t-butyl 3-acetoxymethyl-7α-methoxy-3-cephem-4-carboxylate (95570-83-5) → 4-(tert-butoxycarbonyl)benzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide (128472-66-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1021/jm00171a029

Reference yield:

7-Aminocephalosporanic acid (957-68-6) → 4-(tert-butoxycarbonyl)benzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide (128472-66-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With perchloric acid; 3-chloro-benzenecarboperoxoic acid; isopentyl nitrite;

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

Downstream raw materials:

4-carboxybenzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene carboxylate 5,5-dioxide