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

Article abstract of DOI:10.1016/0008-6215(95)00321-5

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-e nitols (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 separable (Z)-1-aryl-6-O-(tert-butyldimethylsilyl)1,2-dideoxy-3,4-O-isopropylide ne-D-arabino-hex-1-enitols 8a-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 -glucopyranosylarenes 10a-c. Full deprotection of compounds 10a-c and then O-acetylation led to compounds 11a-c, which on treatment with tributyltin hydride-azobisisobutyronitrile yielded the title compounds (12a-c).