@article { ISI:000296036700009,
	title = {Structural, Mechanistic, and Computational Analysis of the Effects of Anomeric Fluorines on Anomeric Fluoride Departure in 5-Fluoroxylosyl Fluorides},
	journal = {JOURNAL OF THE AMERICAN CHEMICAL SOCIETY},
	volume = {133},
	number = {40},
	year = {2011},
	month = {OCT 12},
	pages = {15826-15829},
	abstract = {The effects of fluorine substitution at the C-5 center of pyranosyl fluorides on the reactivity at the C-1 anomeric center was probed by studying a series of 5-fluoroxylosyl fluoride derivatives. X-ray structures of their per-O-acetates detailed the effects on the ground-state structures. First-order rate constants for spontaneous hydrolysis, in conjunction with computational studies, revealed that changes in the stereochemistry of the 5-fluorine had minimal effects on the solvolysis rate constants and that the observed rate reductions were broadly similar to those caused by additional fluorine substitution at C-1 but significantly less than those due to substitution at C-2. Differences in the trapping behavior of 5- versus 2-fluoro-substituted glycosyl fluorides with alpha- and beta-glycosidases arise more from differences in steric effects and hydrogen-bonding interactions than from intrinsic reactivity differences.},
	issn = {0002-7863},
	doi = {10.1021/ja204829r},
	author = {Lee, Seung Seo and Greig, Ian R. and Vocadlo, David J. and McCarter, John D. and Patrick, Brian O. and Withers, Stephen G.}
}
