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

Base Information

• Chemical Name: diphenylmethyl (2S,3R,5R)-3-formyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate
• CAS No.: 188249-92-5
• Molecular Formula: C₂₁H₁₉NO₆S
• Molecular Weight: 413.451
• Mol file: 188249-92-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about diphenylmethyl (2S,3R,5R)-3-formyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 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: 76.0%

diphenylmethyl (2S,3S,5R)-3-hydroxymethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate, 4,4-dioxide + pyrographite (7440-44-0) → 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)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane;

Reference yield: 76.0%

benzhydryl 2β-hydroxymethyl-1,1-dioxopenicillanate (182750-65-8) → 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)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 23h;

DOI:10.1016/j.bmc.2005.02.020

Reference yield:

benzhydryl 2β-(chloroacetoxy)methyl-1,1-dioxo-penicillanate (182750-64-7) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: thiourea / ethanol

2: 76 percent / pyridinium chlorochromate / CH₂Cl₂ / 23 h / 20 °C

With thiourea; pyridinium chlorochromate; In ethanol; dichloromethane;

DOI:10.1016/j.bmc.2005.02.020

upstream raw materials:

benzhydryl 2β-hydroxymethyl-1,1-dioxopenicillanate

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

pyrographite

6-bromopenicillanic acid

Downstream raw materials:

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

(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

(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

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