120316-48-5Relevant academic research and scientific papers
Stereoselective synthesis of 2-deoxy-β-glycosides from glycal precursors. 1. Stereochemistry of the reactions of D-glucal derivatives with phenylsulfenyl chloride and phenylselenenyl chloride
Roush, William R.,Sebesta, David P.,Bennett, Chad E.
, p. 8825 - 8836 (2007/10/03)
The stereoselectivity of the reactions of D-glucal derivatives with PhSCl and PhSeCl is dependent on the presence of an electronegative heteroatom substituent at C(6) and the nature of the functionality at C(4). The C(6)-substituent influences the conformational preferences of the D- glucal derivatives, and greatest stereoselectivity is obtained with those glycals that preferentially exist in the inverted 5H4 half-chair conformation 28b. A polar substituent at C(4) increases the selectivity by stabilizing the episulfonium/episelenonium ion intermediates 31b and 33.
SELENIUM-MEDIATED GLYCOSIDATIONS: A SELECTIVE SYNTHESIS OF β-2-DEOXYGLYCOSIDES
Perez, Michel,Beau, Jean-Marie
, p. 75 - 78 (2007/10/02)
1,2-Trans diequatorial acetoxy-selenides are selectively prepared from glycals.Their activation by trimethylsilyl trifluoromethanesulfonate in the presence of sugar alcohols followed by reductive deselenation leads to an efficient access to Β-2-deoxyglyco
