578713-84-5Relevant academic research and scientific papers
Stereoselective synthesis of C-glycosides from carboxylic acids: The tandem Tebbe-Claisen approach
Godage, H. Yasmin,Chambers, David J.,Evans, Graham R.,Fairbanks, Antony J.
, p. 3772 - 3786 (2003)
A variety of β- or α-C-glycosides may be readily accessed in an entirely stereoselective fashion from esters derived from the reaction of carboxylic acids and 3-hydroxy glycals, by way of a tandem reaction sequence of Tebbe methylenation and Claisen rearrangement. Though of wide scope, for example allowing the synthesis of 1-6 linked C-disaccharides, the methodology does not currently allow the synthesis of C-glycosyl α-amino acids.
Synthesis of α-C-glycosides via tandem Tebbe methylenation and Claisen rearrangement
Godage, H. Yasmin,Fairbanks, Antony J.
, p. 3631 - 3635 (2007/10/03)
A variety of α-C-glycosides may be accessed in an entirely stereoselective fashion from 3-OH glycal esters, by way of the tandem reaction sequence of Tebbe methylenation and Claisen rearrangement. In contrast with previous studies in the corresponding β-series, careful control of conditions for Claisen rearrangement is required in order to avoid loss of integrity of anomeric stereochemistry; thermal rearrangements are best carried out in xylene in a sealed tube.
