1287204-71-0

Basic information

• Product Name: (1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-(trimethylsilyloxy)cyclohexanecarboxylate
• Synonyms: (1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-(trimethylsilyloxy)cyclohexanecarboxylate
• CAS NO: 1287204-71-0
• Molecular Weight: 400.55
• Mol File: 1287204-71-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-(trimethylsilyloxy)cyclohexanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-(trimethylsilyloxy)cyclohexanecarboxylate(1287204-71-0)
• EPA Substance Registry System: (1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-(trimethylsilyloxy)cyclohexanecarboxylate(1287204-71-0)

Safety Data

• Hazardous Substances Data: 1287204-71-0(Hazardous Substances Data)

Upstream product

• 127604-94-8 3-Cyclohexene-1-carboxylic acid (S)-pantolactone ester 
• 109667-78-9 N-(4-chloro-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl)acetamide 
• 5709-98-8 (R)-cyclohex-3-enecarboxylic acid 
• 1287204-68-5 (1R,3S,5S,6S)-ethyl 5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptane-3-carboxylate 
• 1287204-67-4 ethyl (5S)-5-((tert-butoxycarbonyl)amino)cyclohex-3-ene-1-carboxylate 
• 1287204-66-3 (1R,5S)-ethyl 5-(N-(tert-butoxycarbonyl)-4-nitrophenylsulfonamido)cyclohex-3-enecarboxylate 
• 1287204-65-2 (1R,5R)-ethyl 5-hydroxycyclohex-3-enecarboxylate 
• 75-77-4 chloro-trimethyl-silane 
• 1287204-69-6 (1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate 
• 119719-61-8 (1R,4R,5R)-4-iodo-6-oxabicyclo[3.2.1]octane-7-one 

Downstream Products

• 1287204-76-5 (3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohex-1-enecarboxylate 
• 1287204-75-4 (3R,4R,5S)-ethyl-4-azido-5-(tert-butoxycarbonylamino)-3-hydroxycyclohex-1-enecarboxylate 
• 367252-68-4 (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 204255-11-8 oseltamivir phosphate 
• 1287204-73-2 (3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxy-1-(phenylselanyl)cyclohexanecarboxylate 

Relevant articles and documents

Enantioselective synthesis of oseltamivir phosphate

The key steps in the enantioselective synthesis of Tamiflu include an asymmetric Diels-Alder reaction, Mitsunobu inversion using Fukuyama modified Weinreb reagent, carbamate directed epoxidation. Epoxide opening with trimethylsilyl azide furnished a 3:1 mixture of regioisomers that converged to afford the same aziridine. Attempted preparation of the unsaturated ester regioselectively using 2-iodoxybenzoic acid (IBX) following Nicolaou's protocol failed. The unsaturated ester was prepared by phenylselenylation followed by selenoxide elimination.