174413-97-9

Upstream product

• 174413-85-5 tert-Butyl-((3aR,4R,6S,7S,7aS)-7-iodo-2,2-dimethyl-6-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy)-dimethyl-silane 
• 108-24-7 acetic anhydride 
• 174512-52-8 (R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(4R,5R)-2,2-dimethyl-5-((E)-styryl)-[1,3]dioxolan-4-yl]-ethanol 

Downstream Products

• 142697-95-8 (3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-hexopyranosyl)benzene 

Relevant academic research and scientific papers

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-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).