An efficient construction of 1, 2-trans-β-glycosidic linkages capitalizing on glycopyranosyl N, N, N′, N′-tetramethylphosphroamidates as shelf-stable glycosyl donors

S Hashimoto, Y Yanagiya, T Honda, H Harada…

Index: Hashimoto; Yanagiya; Honda; Harada; Ikegami Tetrahedron Letters, 1992 , vol. 33, # 24 p. 3523 - 3526

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Citation Number: 45

Abstract

Abstract A highly stereocontrolled 1, 2-trans-β-glycosidation reaction with or without neighbouring group participation has been developed by using benzyl-or benzoyl-protected glycopyranosyl N, N, N', N'-tetramethylphosphoroamidates as shelf-stable glycosyl donors in the presence of trimethylsilyl trifluoromethanesulfonate or boron trifluoride etherate. Several notable features of the present method not observed with the diphenyl phosphate method ...