220662-75-9Relevant academic research and scientific papers
Investigations on leaving group based intra- versus intermolecular glycoside bond formation
Scheffler, G?tz,Behrendt, Michael E.,Schmidt, Richard R.
, p. 3527 - 3539 (2007/10/03)
Ligation of the glyscosyl donor to the glycossyl acceptor through th eleaving group was performed with the aim of enforcing glycoside bond formation by an intramolecular (1.x)-shift. To this end, systheses of alkoxypropenly (27a and b), and 7-alkoxy-4-oxaheptadienly thioglucopyranoside derivatives (35a, b and d) were carried out. Thier activation with thiophilic systems gave the expected glucopyranosides 5a, b and d in up to high chemical yields, yet modest anomeric control. Competition experiments showed that an intermolecular reaction course is favored in these reactions, although model considerations imply that convenient intramolecular (1,3)-, (1,4)- (1,5)-, and (1,9)-shifts, respectively, of the glycosyl donor to the acceptor are possible.
Decarboxylative glycosylation reaction - Intra- versus intermolecular reaction course
Scheffler, Goetz,Schmidt, Richard R.
, p. 2943 - 2946 (2007/10/03)
Mixed glycosyl carbonates are transformed under acid catalysis into glycosides. Competition experiments with equal amounts of carbonates 5 and 6 led to complete scrambling of the glycosyl donor and acceptor moieties: not only the expected glycosides 7 and
