Non-glycosidic azides of D-altro- and D-gulopyranose

Starting with methyl 2-O-cyclohexylcarbamoyl-3,4-O-(2,2,2-trichloroethylide ne)-alpha -D-altropyranoside side (I), methyl 4-O-cyclohexylcarbamoyl-2,3-O -(2,2,2-trichloroethylidene)-beta -n-gulopyranoside (12), and methyl 6-O-cy clohexylcarbamoyl-2,3-O-(2,2,2-trichloroethylidene)-beta -D-gulopyranoside (21), the 6-azido-6-deoxyaltroses 4, 6, 11, the 6-azido-6-deoxy-D-gulose 14 , the 4-azido-4,6-dideoxy-D-gulose 20, and the 4-azido-4-deoxy-D-gulose 26 were synthesised via iodinated or tosylated precursors. Additionally, two g luco-configured azides, the 3-azido-3,6-dideoxy-D-glucose (19) and the 3-az ido-3-deoxy-D-glucose (25), were obtained besides the desired 4-azido-4-deo xy-D-gulosides 20 and 26, when methyl 6-deoxy-4-O-tosyl-beta -D-gulopyranos ide (18) and methyl 6-O-cyclohexylcarbamoyl-4-O-tosyl-beta -D-gulopyranosid e, respectively, were reacted with sodium azide. An X-ray analysis is prese nted for methyl 2,4-di-O-acetyl-3-azido-3,6-dideoxy-beta -D-glucose (19).