24774-28-5Relevant academic research and scientific papers
Anomeric O-Alkylation, 11. Anomeric O-Alkylation of O-Unprotected Hexoses and Pentoses - Convenient Synthesis of Decyl, Benzyl, and Allyl Glycosides
Klotz, Wolfgang,Schmidt, Richard R.
, p. 683 - 690 (2007/10/02)
The 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 overal 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.Key Words: Aldoses, O-unprotected, glycoside formation / Anomeric oxides, alkylation / Alkylating agents, didecyl sulfate, benzyl bromide, allyl bromide / α-D-galacto-furanosides
