Anomeric O‐alkylation, 11. Anomeric O‐Alkylation of O‐Unprotected Hexoses and Pentoses – Convenient Synthesis of Decyl, Benzyl, and Allyl Glycosides

Abstract

AbstractThe base‐promoted reaction of O‐unprotected aldoses 1–6 with didecyl sulfate in DMPU affords decyl glycosides 1aα–6aα and 1aβ, 3aβ–6aβ in good overall yields. Similarly, the treatment of O‐unprotected hexoses 1–4 and pentoses 5 and 6 with benzyl bromide and allyl bromide yields after subsequent O‐acetylation monosaccharides 1cα–6cα, 1cβ, 3cβ–6cβ and 1dα–6dα, 1dβ, 3dβ–6dβ, respectively. The regio‐ and stereoselectivity in these reactions was determined by 1H‐NMR spectroscopic data of the O‐acetylated derivatives.