AN EFFICIENT CONSTRUCTION OF 1,2-TRANS-BETA-GLYCOSIDIC LINKAGES CAPITALIZING ON GLYCOPYRANOSYL N,N,N',N'-TETRAMETHYLPHOSPHOROAMIDATES AS SHELF-STABLE GLYCOSYL DONORS

被引:41
作者
HASHIMOTO, S [1 ]
YANAGIYA, Y [1 ]
HONDA, T [1 ]
HARADA, H [1 ]
IKEGAMI, S [1 ]
机构
[1] TEIKYO UNIV,FAC PHARMACEUT SCI,SAGAMIKO,KANAGAWA 19901,JAPAN
关键词
D O I
10.1016/S0040-4039(00)92679-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly stereocontrolled 1,2-trans-beta-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 are also described.
引用
收藏
页码:3523 / 3526
页数:4
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