A highly stereoselective β-(1→4)-glycosidic bond formation by reductive cleavage of cyclic orthoesters

Autor: Iimori, Takamasa, Ohtake, Hiro, Ikegami, Shiro
Zdroj: Tetrahedron Letters; January 1997, Vol. 38 Issue: 19 p3415-3418, 4p
Abstrakt: Sterically congested glycosides, glycosyl-β-(1→4)-glycosides, were stereoselectively synthesized by reduction of glycosidic spiro-orthoesters with LiAlH 4AlCl 3. This novel transformation is especially valuable when it is applied to the preparation of mannosyl-β-(1→4)-glycoside which must be one of the most difficult tasks in carbohydrate chemistry.
Databáze: Supplemental Index