benzyl (2S)-6-diazo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Base Information

• Chemical Name: benzyl (2S)-6-diazo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS No.: 15058-70-5
• Molecular Formula: C₁₅H₁₅N₃O₃S
• Molecular Weight: 317.368
• Mol file: 15058-70-5.mol

Synonyms:benzyl (2S)-6-diazo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Chemical Property of benzyl (2S)-6-diazo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S)-6-diazo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

There total 6 articles about benzyl (2S)-6-diazo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[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: 90.0%

benzyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (3956-31-8,49626-54-2,64519-71-7) → 6-diazopenicillanic acid benzyl ester (15058-70-5)

Guidance literature:

With ethyl nitrite; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1016/j.tet.2012.03.022

Reference yield:

benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (1254-56-4) → 6-diazopenicillanic acid benzyl ester (15058-70-5)

Guidance literature:

Multi-step reaction with 2 steps

1: N₂O₄, AcONa / CH₂Cl₂ / -5 °C

2: CH₂Cl₂ / 4 h / Heating

With sodium acetate; dinitrogen tetraoxide; In dichloromethane;

Reference yield:

(2S,5R,6R)-6-amino-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane p-toluenesulfonic acid (19912-14-2) → 6-diazopenicillanic acid benzyl ester (15058-70-5)

Guidance literature:

With toluene-4-sulfonic acid; sodium nitrite;

DOI:10.1016/0040-4020(95)00637-N

upstream raw materials:

benzyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

C₂₃H₂₃N₃O₅S

(2S,5R,6R)-6-amino-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane p-toluenesulfonic acid

benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Downstream raw materials:

6α-iodo-penicillanic acid benzyl ester

Benzyl 6α-bromopenicillanate

benzyl 6,6-dibromopenicillanate

(6'R)-5-carbamoyl-3',3'-dimethyl-7'-oxo-2,4-dihydro-(5'tH,6'rN)-spiro[pyrazole-3,6'-(4-thia-1-aza-bicyclo[3.2.0]heptane)]-2't-carboxylic acid benzyl ester