%0 Journal Article
%A Bhat, Abhijit S.
%A Gervay-Hague, Jacquelyn
%D 2001
%T Efficient Syntheses of β-Cyanosugars
Using Glycosyl Iodides Derived from
Per-O-silylated Mono- and Disaccharides
%U https://acs.figshare.com/articles/journal_contribution/Efficient_Syntheses_of_-Cyanosugars_Using_Glycosyl_Iodides_Derived_from_Per-_i_O_i_-silylated_Mono-_and_Disaccharides/3739347
%R 10.1021/ol0160405.s001
%2 https://acs.figshare.com/ndownloader/files/5831115
%K Efficient Syntheses
%K THF
%K CoCl 2
%K NaBH 4
%K Glycosyl Iodides Derived
%K H 2 O
%K Disaccharides Reported
%K tetrabutylammonium cyanide
%K trimethylsilyl glycosides
%K TMSI
%K aminomethyl glycosides
%K silylated Mono
%X Reported herein is a general method for the efficient syntheses of a variety of β-cyano glycosides through the activation of per-O-trimethylsilyl
glycosides with TMSI to form α-glycosyl iodides, which undergo SN2-type displacement when treated with tetrabutylammonium cyanide. The
cyanoglycosides were reduced under mild conditions using NaBH4 in the presence of catalytic CoCl2(H2O)6 in THF/H2O to give the corresponding
aminomethyl glycosides.
%I ACS Publications