Glycosidation, 15. — Anticancer agents, 11. Development of selective anticancer agents synthesis of acetal‐β‐glucosides from cytotoxic alcohols

Abstract

AbstractThe reaction of trimethylsilyl 2,3,4,6‐tetra‐O‐acetyl‐β‐D‐glucopyranoside 7 with hexanal and the trimethylsilyl ethers 9a–c of cytotoxic alcohols 4a–c in the presence of catalytic amounts of TMS triflate yields the acetal‐β‐glucosides 10a–c. In a similar way, the acetal‐α‐glucosides 12a, b are obtained from 8, hexanal, and 9a, b. In addition, the highly acid‐sensitive acetal‐β‐glucoside 13 is synthesized from 7, acetone, and 9a. Deacetylation of 10a, 10b, and 13 by solvolysis affords the deprotected acetal‐β‐glucosides 11a, 11b, and 14, respectively, which will be tested as selective anticancer agents.