1443055-49-9

Basic information

• Product Name: (3R,4R,5S)-ethyl 4-acetylamino-3-(pentan-3-yloxy)-5-(2,2,2-trichloroacetamido)cyclohex-1-enecarboxylate
• Synonyms: (3R,4R,5S)-ethyl 4-acetylamino-3-(pentan-3-yloxy)-5-(2,2,2-trichloroacetamido)cyclohex-1-enecarboxylate
• CAS NO: 1443055-49-9
• Molecular Weight: 457.782
• Mol File: 1443055-49-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3R,4R,5S)-ethyl 4-acetylamino-3-(pentan-3-yloxy)-5-(2,2,2-trichloroacetamido)cyclohex-1-enecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R,5S)-ethyl 4-acetylamino-3-(pentan-3-yloxy)-5-(2,2,2-trichloroacetamido)cyclohex-1-enecarboxylate(1443055-49-9)
• EPA Substance Registry System: (3R,4R,5S)-ethyl 4-acetylamino-3-(pentan-3-yloxy)-5-(2,2,2-trichloroacetamido)cyclohex-1-enecarboxylate(1443055-49-9)

Safety Data

• Hazardous Substances Data: 1443055-49-9(Hazardous Substances Data)

Upstream product

• 204254-96-6 (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester 
• 99418-52-7 isopropyl 2,2,2-trichloroacetimidate 
• 1268086-96-9 ethyl (3R,4R,5R)-4,5-acetylimino-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate 
• 332047-23-1 (3R,4S,5R)-ethyl 5-acetylamino-4-methanesulfonyloxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 1443055-47-7 (3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 

Downstream Products

• 196618-13-0 oseltamivir 

Relevant articles and documents

A novel azide-free asymmetric synthesis of oseltamivir phosphate (Tamiflu) starting from Roche's epoxide

A novel azide-free asymmetric synthesis of oseltamivir phosphate 1 (Tamiflu) starting from Roche's epoxide is described. Roche epoxide 2 was converted into N-acetyl aminoalcohol 3 in 95% yield via a BF3· OEt2-catalyzed epoxide-opening with acetonitrile as a nucleophile. Compound 3 was then transformed into a methanesulfonate 4 in 98% yield. Compound 4 was converted into aziridine 5 in 91% yield. Aziridine 5 was subsequently converted into oseltamivir phosphate 1 via two paths (a and b). In the path a, compound 5 underwent aziridine-opening with diallylamine as a nucleophile to afford compound 7 in 93% yield; compound 7 could then be converted into oseltamivir phosphate 1 in 88% yield. In path b, compound 5 underwent aziridine-opening with isopropyl 2,2,2-trichloroacetimidate as a nucleophile to afford compound 8 in 94% yield, which was then converted into oseltamivir phosphate 1 in 82% yield.