A HIGHLY STEREOSELECTIVE BETA-(1-]4)-GLYCOSIDIC BOND FORMATION BY REDUCTIVE CLEAVAGE OF CYCLIC ORTHOESTERS

Authors
IIMORI T OHTAKE H IKEGAMI S
Citation
T. Iimori et al., A HIGHLY STEREOSELECTIVE BETA-(1-]4)-GLYCOSIDIC BOND FORMATION BY REDUCTIVE CLEAVAGE OF CYCLIC ORTHOESTERS, Tetrahedron letters, 38(19), 1997, pp. 3415-3418
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
19
Year of publication
1997
Pages
3415 - 3418
Database
ISI
SICI code
0040-4039(1997)38:19<3415:AHSBBF>2.0.ZU;2-N
Abstract
Sterically congested glycosides, glycosyt-beta-(1-->4)-glycosides, wer e stereoselectively synthesized by reduction of glycosidic spiro-ortho esters with LiAlH4-AlCl3. This novel transformation is especially valu able when it is applied to the preparation of mannosyl-beta-(1-->4)-gl ycoside which must be one of the most difficult tasks in carbohydrate chemistry. (C) 1997 Elsevier Science Ltd.