A convenient synthesis for anomeric 2-thioglucobioses, 2-thiokojibiose and 2-thiosophorose.
2-S-alpha-D-Glucopyranosyl-2-thio-D-glucopyranose (2-thiokojibiose, 8) and 2-S-beta-D-glucopyranosyl-2-thio-D-glucopyranose (2-thiosophorose, 14) were conveniently prepared by SN2 reaction of the corresponding anomers of 2,3,4,6-tetra-O-acetyl-1-thio-D-glucopyranose with 1,3,4,6-tetra-O-acetyl-2-O-tri-flyl-beta-D-mannopyranose, followed by a deprotection sequence for the anomeric acetate involving conversion into the 1-propenyl glycosides. Alkaline O-deacetylation was followed by smooth hydrolysis of the propenyl group at pH approximately 2.
Defaye
J
J
CNRS, Département de Recherche Fondamentale sur la Matière Condensée/SESAM, Centre d'Etudes de Grenoble, France.
Guillot
J M
JM
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009904:Optical Rotation; D016339:Spectrometry, Mass, Fast Atom Bombardment
D004187:Disaccharides; D007202:Indicators and Reagents; C086800:2-thiokojibiose; C086801:2-thiosophorose