6α-isocyanopenicillanate

Base Information

• Chemical Name: 6α-isocyanopenicillanate
• CAS No.: 65058-78-8
• Molecular Formula: C₁₆H₁₆N₂O₃S
• Molecular Weight: 316.381

Synonyms:6α-isocyanopenicillanate

Chemical Property of 6α-isocyanopenicillanate

Chemical Property:

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Technology Process of 6α-isocyanopenicillanate

There total 2 articles about 6α-isocyanopenicillanate 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:

6β-formylamino-penicillanic acid benzyl ester (53628-26-5) + phosgene (75-44-5) → 6α-isocyanopenicillanate (65058-78-8)

Guidance literature:

With 4-methyl-morpholine; In ice-water; dichloromethane; ethyl acetate; petrol;

Reference yield:

→ 6α-isocyanopenicillanate (65058-78-8)

Guidance literature:

Benzyl 6β-formamidopenicillanat, NEt3/CH2Cl2, Phosgen;

Reference yield: 50.0%

bromoacetic acid tert-butyl ester (5292-43-3) + 6α-isocyanopenicillanate (65058-78-8) → 2-((1R,5R)-1-tert-Butoxycarbonylmethyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-2-enoic acid benzyl ester (88065-64-9) + benzyl 6α-t-butoxycarbonylmethyl-6β-isocyanopenicillanate (88065-63-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/S0040-4020(01)92141-6

upstream raw materials:

6β-formylamino-penicillanic acid benzyl ester

phosgene

Downstream raw materials:

3-methyl-2-((1S)-1-methylsulfanyl-7-oxo-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-2-enoic acid benzyl ester

2-[(1R)-1-(2-benzyloxycarbonyl-ethyl)-7-oxo-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl]-3-methyl-but-2-enoic acid benzyl ester

2-[acetyl-((E)-5-oxo-thiazol-4-ylidenemethyl)-amino]-3-methyl-but-2-enoic acid benzyl ester

2-((1R)-3-chloro-7-oxo-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-2-enoic acid benzyl ester

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