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• W2164516775 abstract "The synthesis and characterization of the anomeric pairs of the per-O-acetylaldohexopyranosyl cyanides of d-galactose, l-fucose, d-glucose, and d-mannose, as well as of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl cyanide, are described. Cyanation of the readily available, per-O-acetylaldohexopyranosyl bromides with mercuric cyanide in nitromethane, and subsequent purification, gave the corresponding, crystalline glycosyl cyanides with a high degree of 1,2-trans stereoselectivity. Thus, per-O-acetylated aldohexopyranosyl cyanides of the 1,2-trans configuration were obtained in yields ranging from 20 to 79%, whereas the corresponding 1,2-cis anomers were obtained in yields of ⩽8.4%, the ratios of the 1,2-trans: 1,2-cis anomers so prepared being ⩾8.5:1. The principal by-products of these irreversible, cyanation reactions were the per-O-acetylated 1,2-O-[1-(exo- and endo-cyano)ethylidene]aldohexopyranoses, obtained in yields of up to 40%. The structural assignments of the per-O-acetylaldohexopyranosyl cyanides were unequivocally established by elemental analysis, chemical transformation, vibrational spectroscopy, and 13C- and 1H-nuclear magnetic resonance spectroscopy. Correlations between the physical properties and the anomeric configurations of these C-aldohexopyranosyl compounds are described." @default.
• W2164516775 created "2016-06-24" @default.
• W2164516775 creator A5052816975 @default.
• W2164516775 creator A5059355678 @default.
• W2164516775 date "1984-09-01" @default.
• W2164516775 modified "2023-10-14" @default.
• W2164516775 title "Synthesis and characterization of some anomeric pairs of per-O-acetylated aldohexopyranosyl cyanides (per-O-acetylated 2,6-anhydroheptononitriles). On the reaction of per-O-acetylaldohexopyranosyl bromides with mercuric cyanide in nitromethane" @default.
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• W2164516775 doi "https://doi.org/10.1016/0008-6215(84)85065-x" @default.
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