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Synlett 1991; 1991(3): 168-170
DOI: 10.1055/s-1991-20665
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Glycoside Bond Formation via Anomeric O-Alkylation: How Many Protective Groups Are Required?

Richard R. Schmidt* , Wolfgang Klotz
  • *Fakultät Chemie, Universität Konstanz, Postfach 5560, D-7750 Konstanz, Germany
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Publikationsdatum:
07. März 2002 (online)

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6-O-Unprotected glucose 1, 2-O-unprotected glucose 3, 2,3,4-O-unprotected glucose 6, and 2,3,2′,3′ ,4′-O-unprotected lactose 10 furnished in presence of sodium hydride as base and decyl trifluoromethanesulfonate as alkylating agent exclusively anomeric O-alkylation products 2, 4, 7, and 11, respectively, when dichloromethane or toluene were used as solvents. In tetrahydrofuran as solvent, in addition, participation of the solvent in the anomeric O-alkylation process was observed. Thus, it was found that O-protection is only required to facilitate solubility of the starting materials but not for regio- and stereoselective anomeric O-alkylation.