(2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester

Base Information

• Chemical Name: (2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester
• CAS No.: 182750-66-9
• Molecular Formula: C₂₁H₁₉NO₇S
• Molecular Weight: 429.45
• Mol file: 182750-66-9.mol

Synonyms:(2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester

Chemical Property of (2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester

Chemical Property:

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester

There total 8 articles about (2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl 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: 27.0%

benzhydryl 2β-hydroxymethyl-1,1-dioxopenicillanate (182750-65-8) → (2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester (182750-66-9)

Guidance literature:

With potassium permanganate; tetrabutylammomium bromide;

DOI:10.7164/antibiotics.49.944

Reference yield:

diphenylmethyl (2S,3R,5R)-3-formyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate (188249-92-5) → (2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester (182750-66-9)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃; for 1h;

DOI:10.1128/AAC.06099-11

Reference yield:

benzhydryl 2β-(chloroacetoxy)methyl-1,1-dioxo-penicillanate (182750-64-7) → (2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester (182750-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / thiourea / ethanol / Heating

2: 27 percent / KMnO₄, tetrabutylammonium bromide

With potassium permanganate; tetrabutylammomium bromide; thiourea; In ethanol;

DOI:10.7164/antibiotics.49.944

upstream raw materials:

benzhydryl 2β-hydroxymethyl-1,1-dioxopenicillanate

benzhydryl 2β-(chloroacetoxy)methyl-1,1-dioxo-penicillanate

diphenylmethyl (2S,3R,5R)-3-formyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

6-Aminopenicillanic Acid

Downstream raw materials:

(2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,3R,5R)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,3R,5R)-3-(4-Benzyl-piperazine-1-carbonyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester