An expeditious route to the synthesis of adenophostin A

Article abstract of DOI:10.1016/0040-4039(96)00632-6

Glycosylation of 1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranose (8) with ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-α/β-D-glucopyranoside (7) under the agency of N-iodosuccinimide and trifluoromethanesulfonic acid (cat.) afforded α-linked dimer 10 in 95% yield. Vorbruggen-type condensation of 12, obtained by deacetonation of 10 and subsequent acetylation, with bis-trimethylsilyl N⁶-benzoyl adenine gave adenosyl glucoside 13. Protective group manipulations followed by phosphorylation furnished, after deprotection, homogeneous 2 in high overall yield.