34980-26-2Relevant academic research and scientific papers
A method for the synthesis of C-(2-deoxy-β-glycosyl) arenes
Khan, Abu T.,Ahmed, Wasim,Schmidt, Richard R.
, p. 277 - 286 (1996)
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).
