On the stereoselectivity of glycosidation of thiocyanates, thioimidates, and thioglycosides.
Comparative side-by-side glycosylation studies demonstrated that glycosyl thiocyanates, thioimidates, and thioglycosides provide comparative stereoselectivities in glycosylations. Very high α-stereoselectivity that was previously recorded for glycosyl thiocyanates can be achieved, but only if glycosyl acceptors are equipped with electron-withdrawing acyl substituents. Partially benzylated glycosyl acceptors provided relatively modest stereoselectivity, which was on a par with other common glycosyl donors. Accordingly, thioimidates and thioglycosides showed high stereoselectivity similarly to that of thiocyanates with different classes of acylated primary and secondary glycosyl acceptors.
Kaeothip
Sophon
S
Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, MO 63121, USA.
Akins
Steven J
SJ
Demchenko
Alexei V
AV
D006031:Glycosylation; D007096:Imidoesters / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013861:Thiocyanates / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry*
D007096:Imidoesters; D013861:Thiocyanates; D013865:Thioglycosides