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Cyano sugars 2. synthesis of hexo pyranosyl cyanides by reaction of glycals with tri methylsilyl cyanide

, : Cyano sugars 2. synthesis of hexo pyranosyl cyanides by reaction of glycals with tri methylsilyl cyanide. Tetrahedron 39(9): 1617-1620

3,4,6-Tri-O-acetyl-O-glucal and 2,3,4,6-tetra-O-acetyl-2-hydroxy-D-glucal reacted with Me3SiCN in the presence of a Lewis acid (SnCl4, BF3) as catalyst to give anomeric pairs of 2,3-dideoxy-hex-2-enopyranosyl cyanides and 3-deoxy-hex-2-enopyranosyl cyanides. These 2,3-unsaturated glycopyranosyl cyanides were hydrogenated over Pd/C to afford the corresponding 2,3-dideoxy- and 3-deoxy-hexopyranosyl cyanides. [Glycosyl cyanides are intermediates for the synthesis of C-glycosyl derivatives such as C-nucleoside antibiotics.].


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Waddell, C., 1993: Testing for HIV infection among heterosexual, bisexual and gay men. This paper answers the questions: who is and is not tested for human immunodeficiency virus (HIV) antibodies, why, where are they tested, and what do they find difficult about the testing process? The data came from two samples of sexually active...

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