Anomeric configuration-directed diastereoselective C-C bond formation in vinyl sulfone-modified carbohydrates: a general route to branched-chain sugars.
[structure: see text] This is the first report on the diastereoselective addition of carbon nucleophiles to vinyl sulfone-modified hex-2-enopyranosides and pent-2-enofuranosides. Nucleophiles add to the C-2 position from a direction opposite to that of the disposition of the anomeric methoxy group. This novel concept of anomeric configuration-directed stereocontrolled carbon-carbon bond formation in vinyl sulfone-modified carbohydrates is general in nature and has been implemented in the synthesis of new hexopyranosyl and pentofuranosyl branched-chain sugars and densely functionalized carbohydrates.
Sanki
Aditya K
AK
Organic Chemistry Division (Synthesis), National Chemical Laboratory, Pune 411 008, India.
Suresh
Cheravakkattu G
CG
Falgune
Usha D
UD
Pathak
Tanmaya
T
D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D018360:Crystallography, X-Ray; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
D002241:Carbohydrates; D013450:Sulfones; C009873:divinyl sulfone