1246760-20-2

Upstream product

• 1246760-19-9 2-((2R,4aR,6S,7R,8aS)-2-phenyl-7-((E)-2-(phenylsulfonyl)vinyloxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)acetaldehyde 

Downstream Products

• 1246760-29-1 (2R,4aS,6R,7S,8aR)-7-hydroxy-6-(hydroxymethyl)-2-(phenylsulfonylmethyl)hexahydropyrano[3,2-b]pyran-3(2H)-one benzylidene acetal 
• 1246760-21-3 (2R,3R,4aS,6R,7S,8aR)-7-hydroxy-6-(hydroxymethyl)-2-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3-yl acetate benzylidene acetal 
• 1246760-27-9 (2R,3S,4aR,6R,7R,8aS)-7-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)-6-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3-ol benzylidene acetal 

Relevant academic research and scientific papers

SmI2-induced cyclization of (E)- and (Z)-β-alkoxyvinyl sulfones with aldehydes

SmI2-induced reaction of (E)- and (Z)-β-alkoxyvinyl sulfones onto an aldehyde function afforded 2,6-syn-2,3-trans- and 2,6-syn-2,3-cis-tetrahydropyran-3-ols, respectively, via stereoselective cyclization. This reaction was applied to the synthesis of 2-methyl- tetrahydropyran, corresponding to the N-ring of gymnocin-A, and 2-exo-methylene-tetrahydropyran, a key intermediate for convergent synthesis of polycyclic ethers based on the Suzuki-Miyaura reaction.