The cyanation reaction of O-acetylated S-glycosyl phosphorothioates.
The reaction of alpha- and beta-1-S-phosphorothioates of per-O-acetylated monosaccharides (galactose, xylose, glucose) with trimethylsilyl cyanide in the presence of boron trifluoride etherate has been investigated. It has been established that in dichloromethane 1,2-O-cyanoethylidene derivatives of aldoses are formed in high yields. When the reaction was carried out in acetonitrile, peracetylated galactosyl cyanide was formed as the major product.
Kudelska
W
W
Institute of Chemistry, Faculty of Pharmacy, Medical University of Lodz, Poland. kudelska@ich.pharm.am.lodz.pl
D000107:Acetylation; D003486:Cyanides / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009946:Organothiophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D003486:Cyanides; D006027:Glycosides; D009946:Organothiophosphorus Compounds