A METHOD FOR THE SYNTHESIS OF C-(2-DEOXY-BETA-GLYCOSYL)ARENES

2,3:4,5-Di-O-isopropylidene-aldehydo-D-arabinose (2) was converted by a Wittig reaction into a mixture of ,4:5,6-di-O-isopropylidene-D-arabi no-hex-1-enitols (4,5). Selective deprotection of the 5,6-O-isopropyli dene group in compounds 4 and 5 followed by selective silylation at po sition 6 afforded the separable (Z)-1-aryl-6-O-(tert-butyldimethylsily l) deoxy-3,4-O-isopropylidene-D-arabino-hex-1-enitols 8a-d and the cor responding E-isomers (9a-d). Iodonium-ion-induced cyclization of compo unds 8c and 9a-c furnished stereoselectively the o-3,4-O-isopropyliden e-beta-D-glucopyranosylarenes 10a-c. Full deprotection of compounds 10 a-c and then O-acetylation led to compounds 11a-c, which on treatment with tributyitin hydride-azobisisobutyronitrile yielded the title comp ounds (12a-c).