benzyl 6β-penicillanate

Base Information

• Chemical Name: benzyl 6β-penicillanate
• CAS No.: 93553-11-8
• Molecular Formula: C₂₅H₂₅Cl₃N₂O₇S₂
• Molecular Weight: 635.974
• Mol file: 93553-11-8.mol

Synonyms:

Chemical Property of benzyl 6β-penicillanate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 6β-penicillanate

There total 3 articles about benzyl 6β-penicillanate 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: 79.0%

3α-Benzyloxycarbonyl-6β-aminopenam p-toluenesulfonate (93552-73-9) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → benzyl 6β-penicillanate (93553-11-8)

Guidance literature:

With pyridine; In dichloromethane; 1) 0 deg C 2) RT, 1.5 h;

Reference yield:

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(toluene-4-sulfonylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (93552-73-9,102715-50-4) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → C25H25Cl3N2O7S2 (93553-11-8)

Guidance literature:

With pyridine; In dichloromethane;

DOI:10.1016/S0040-4039(01)80822-4

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → benzyl 6β-penicillanate (93553-11-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) CH₂Cl₂, -20 deg C 2) CH₂Cl₂, RT, 70 h

2: 79 percent / pyridine / CH₂Cl₂ / 1) 0 deg C 2) RT, 1.5 h

With pyridine; In dichloromethane;

upstream raw materials:

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(toluene-4-sulfonylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

2,2,2-Trichloroethyl chloroformate

3α-Benzyloxycarbonyl-6β-aminopenam p-toluenesulfonate

p-toluenesulfonyl chloride

Downstream raw materials:

C₂₅H₂₅Cl₃N₂O₈S₂

(2S,4R,6R)-6-Formylamino-3,3-dimethyl-4,7-dioxo-6-(2,2,2-trichloro-ethoxycarbonylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

C₂₅H₂₅Cl₃N₂O₈S₂