1350929-01-9

Upstream product

• 1350929-00-8 C₁₁H₁₄O₇S 
• 1350928-94-7 C₉H₁₂O₆S 
• 101769-63-5 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 

Downstream Products

• 1149345-89-0 ethyl (3R,4R,5R)-4-acetamido-3-(1-ethyl-propoxy)-5-hydroxy-cyclohex-1-ene-1-carboxylate 
• 1350929-05-3 ethyl (3R,4R,5R)-4-acetamido-5-acetoxy-3-(1-ethylpropoxy)-cyclohex-1-ene-1-carboxylate 
• 1350929-02-0 ethyl (3S,4R,5R)-3-azido-5-acetoxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate 

Relevant academic research and scientific papers

Novel asymmetric synthesis of oseltamivir phosphate (Tamiflu) from (-)-shikimic acid via cyclic sulfite intermediates

A novel asymmetric synthesis of oseltamivir phosphate 1 from the naturally abundant (-)-shikimic acid via 3,4-cyclic sulfite intermediate 3 (Scheme 1) is described. Target compound 1 was obtained in 39% overall yield from this nine-step synthesis, and the characteristic step of the synthesis is the regio- and stereospecific nucleophilic substitution with sodium azide at the allylic (C-3) position of 3,4-cyclic sulfite 3. Since the yield of the direct-aziridine-formation from the unprotected dihydroxyl azide 4 was not satisfactory, two improved preparations of the established compound 7 via protected 3,4-cyclic sulfites 10 and 13 (Scheme 2) have been developed. In these two improved preparations, compound 7 was obtained from 3,4-cyclic sulfite 3 in 7-steps in 64% or 62% overall yield, respectively. Copyright