(2S,5R,6S)-3,3-Dimethyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester

Base Information

• Chemical Name: (2S,5R,6S)-3,3-Dimethyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester
• CAS No.: 107668-69-9
• Molecular Formula: C₂₅H₂₆N₂O₈S
• Molecular Weight: 514.556

Synonyms:

Chemical Property of (2S,5R,6S)-3,3-Dimethyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (2S,5R,6S)-3,3-Dimethyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester

There total 3 articles about (2S,5R,6S)-3,3-Dimethyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2,6-dicarboxylic acid 2-benzyl ester 6-methyl 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: 26.0%

(2S,5R,6R)-6-(Hydroxy-methoxy-methyl)-3,3-dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester → (5R)-3,3-dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c,6c-dicarboxylic acid 2-benzyl ester 6-methyl ester (41113-71-7) + (2S,5R,6S)-3,3-Dimethyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester (107668-69-9,107668-70-2)

Guidance literature:

With chromium(VI) oxide; acetic anhydride; In pyridine; for 4h;

DOI:10.1016/S0040-4039(00)84713-9

Reference yield: 24.0%

(2S,5R,6R)-6-(Hydroxy-methoxy-methyl)-3,3-dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester → (2S,5R,6S)-3,3-Dimethyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester (107668-69-9,107668-70-2)

Guidance literature:

With chromium(VI) oxide; acetic anhydride; In pyridine; for 16h;

DOI:10.1016/S0040-4039(00)84713-9

Reference yield:

6β-(phenoxyacetamido)penicillinate (94612-05-2) → (2S,5R,6S)-3,3-Dimethyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester (107668-69-9,107668-70-2)

Guidance literature:

Multi-step reaction with 2 steps

1: silica gel

2: 26 percent / CrO₃, Ac₂O / pyridine / 4 h

With chromium(VI) oxide; acetic anhydride; silica gel; In pyridine;

DOI:10.1016/S0040-4039(00)84713-9

upstream raw materials:

6β-(phenoxyacetamido)penicillinate

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