Is Donor−Acceptor Hydrogen Bonding Necessary for 4,6-O-Benzylidene-directed β-Mannopyranosylation? Stereoselective Synthesis of β-C-Mannopyranosides and α-C-Glucopyranosides
- 1 October 2008
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (21) , 4731-4734
- https://doi.org/10.1021/ol8017038
Abstract
2,3-Di-O-benzyl-4,6-O-benzylidene-thiohexopyranosides, on activation with 1-benzenesulfinyl piperidine and triflic anhydride, react with allyl silanes and stannanes, and with silyl enolethers to give C-glycosides. In the mannose series the β-isomers are formed selectively whereas the glucose series provides the α-anomers. This selectivity pattern parallels that of O-glycoside formation and eliminates the need to consider donor−acceptor hydrogen bonding in the formation of the O-glycosides.Keywords
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