Novel Molecular Clamp Method for Anomeric Stereocontrol of Glycosylation

Masahiro Wakao; Koichi Fukase; Shoichi Kusumoto

doi:10.1055/s-1999-2997

Synlett 1999; 1999(12): 1911-1914
DOI: 10.1055/s-1999-2997

letter

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Novel Molecular Clamp Method for Anomeric Stereocontrol of Glycosylation

Masahiro Wakao^* , Koichi Fukase, Shoichi Kusumoto

^*Department of Chemistry, Graduate School of Science, Osaka University, Machikaneyama 1-1, Toyonaka, Osaka 560-0043, Japan; E-mail: koichi@chem.sci.osaka-u.ac.jp

Abstract

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Stereocontrolled glycosylation is described by using a molecular clamp, which binds a glycosyl donor to an acceptor and controls their spatial arrangement. An α(1 → 4) glycosidic linkage was formed in a good yield with high selectivity by the use of phthaloyl bridge bound to both 6-positions of a glycosyl donor and an acceptor. β-Selective glycosylation was effected by the use of a silyl bridge attached to the same 6-positions of the same glycosyl donor and acceptor. Application of this method to the synthesis of a maltotetraose derivative is also described.

intramolecular glycosylation - stereocontrol - molecular clamp - glycosides - carbohydrate

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