A method for the synthesis of C-(2-deoxy-β-glycosyl) arenes

2,3:4,5-Di-O-isopropylidene-aldehydo-d-arabinose (2) was converted by a Wittig reaction into a mixture of (E/Z)-1-aryl-1,2-dideoxy-3,4:5,6-di-O-isopropylidene-d-arabino-hex-1-enitols (4,5). Selective deprotection of the 5,6-O-isopropylidene group in compounds 4 and 5 followed by selective silylation at position 6 afforded the separate (Z)-l-aryl-6-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-d-arabino-hex-1-enitols8a–d and the corresponding E-isomers (9a–d). Iodonium-ion-induced cyclization of compounds 8c and 9a-c furnished stereoselectively the 6-O-(tert-butyldimethylsilyl)-2-deoxy-2-iodo-3,4-O-isopropylidene-β-d-glucopyranosylarenes10a–c. Full deprotection of compounds 10a–c and the O-acetylation led to compounds 11a–c, which on treatment with tributyltin hydride-azobisisobutyromnitrile yielded and the title compounds (12a–c).