18929-99-2Relevant academic research and scientific papers
α-selective ribofuranosylation of alcohols with ribofuranosyl iodides and triphenylphosphine oxide
Oka, Natsuhisa,Kajino, Rin,Takeuchi, Kaoru,Nagakawa, Haruna,Ando, Kaori
, p. 7656 - 7664 (2014)
Ribofuranosylation of a variety of alcohols with ribofuranosyl iodides in the presence of a base and triphenylphosphine oxide afforded the corresponding α-ribofuranosides with diastereoselectivities ≥ 99:1. This reaction can be carried out under mildly basic conditions and is thus compatible with acid-sensitive functional groups.
Dioxolanylium Ions Derived from Carbohydrates. XI. Aminosugar Formation by trans Opening with the Trichloroacetimidoyl Neighbouring Group
Jacobsen, Steffen
, p. 498 - 504 (2007/10/02)
A variety of benzylidene sugars containing vicinal trichloroacetimidoyl groups have been oxidized by N-bromosuccinimide, to ascertain which structural features are necessary for neighbouring group participation from the iminoester in the opening of the transitory benzoxonium ion.The results indicate that the trichloroacetimidoyl group closely resembles the acyl group in its ability to participate, and that the resulting iminoester is strongly favoured compared to the benzoxonium ion.The outcome of the reaction in these cases is therefore a clean, regiospecific introduction of an amino group into the carbohydrate molecule.
