An efficient synthesis of beta-C-glycosides based on the conformational restriction strategy: Lewis acid promoted silane reduction of the anomeric position with complete stereoselectivity.
[reaction: see text] The reduction of glyconolactols having an anomeric carbon substituent by Et(3)SiH/TMSOTf proceeded with complete stereoselectivity to produce the corresponding beta-C-glycosides when the substrates were conformationally restricted in the (4)C(1)-chair form by a 3,4-O-cyclic diketal or a 4,6-O-benzylidene protecting group. Thus, the efficient construction of beta-C-glycosides was achieved on the basis of the conformation restriction strategy.
Terauchi
Masaru
M
Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
Abe
Hiroshi
H
Matsuda
Akira
A
Shuto
Satoshi
S
D000143:Acids / Q000737:chemistry*; D002236:Carbohydrate Conformation; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000143:Acids; D006027:Glycosides; D012821:Silanes