Journal
CARBOHYDRATE RESEARCH
Volume 345, Issue 15, Pages 2146-2150Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2010.08.003
Keywords
Glycosylation; Stereoselectivity; Protecting groups; Glycosyl donors
Funding
- NSF [CHE-0547566]
- American Heart Association [0855743G]
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Comparative side-by-side glycosylation studies demonstrated that glycosyl thiocyanates, thioimidates, and thioglycosides provide comparative stereoselectivities in glycosylations. Very high alpha-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. (C) 2010 Elsevier Ltd. All rights reserved.
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