1428733-29-2

Upstream product

• 1428733-23-6 tert-butyl (4S,5R)-5-allyl-2,2-dimethyl-4-(3-oxopropyl)oxazolidine-3-carboxylate 
• 1428733-26-9 tert-butyl (4S,5R)-5-allyl-4-(2-formylallyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1428733-27-0 tert-butyl (3aS,7aR)-5-formyl-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo[d]oxazole-3(2H)-carboxylate 
• 1428733-22-5 tert-butyl (4S,5R)-5-allyl-4-(3-hydroxypropyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1428733-21-4 tert-butyl (4S,5R)-1,5-dihydroxyoct-7-en-4-ylcarbamate 
• 1428733-20-3 tert-butyl (S)-2-[(R)-1-hydroxybut-3-enyl]-5-oxopyrrolidine-1-carboxylate 
• 1428733-30-5 (4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylic acid 
• 75-03-6 ethyl iodide 
• 1428733-25-8 tert-butyl (4S,5R)-2,2-dimethyl-5-(2-oxoethyl)-4-(3-oxopropyl)oxazolidine-3-carboxylate 
• 185303-87-1 tert-butyl (S)-2-formyl-5-oxopyrrolidine-1-carboxylate 
• 1298023-90-1 (5S)-N-(tert-butyloxycarbonyl)pyrrolidin-2-one-5-carbothioic acid ethyl ester 
• 53100-44-0 L-N-t-butoxycarbonylpyroglutamic acid 
• 1428733-28-1 tert-butyl (1S,6R)-3-formyl-6-hydroxycyclohex-3-enylcarbamate 

Downstream Products

• 950690-19-4 ethyl (S)-5-((tert-butoxycarbonyl)amino)cyclohexa-1,3-diene-1-carboxylate 
• 1428733-31-6 ethyl (4R,5S)-5-(tert-butoxycarbonylamino)-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate 

Relevant academic research and scientific papers

Formal synthesis of (-)-oseltamivir phosphate

The formal synthesis of (-)-oseltamivir phosphate (Tamiflutm) was accomplished starting from (S)-pyroglutamic acid. The synthesis comprised two carbon-carbon bond forming reactions, the first one being a diastereoselective, indium-mediated allylation of a pyroglutamic aldehyde derivative. However, attempts to effect the second carbon-carbon bond formation - cyclohexene ring closure - using an enol-exo aldolization of a dialdehyde resulted in the formation of a product with the opposite regioselectivity. This shortcoming could be overcome by using a reaction sequence of Mannich methylenation/ring-closing metathesis, which provided the desired regioisomer in high yield. Georg Thieme Verlag Stuttgart.New York.