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A mechanistic study: Nucleophile dependence in glucosylations with glucosyl bromides
Author(s) -
Bowden Tim,
Garegg Per J.,
Maloisel JeanLuc,
Konradsson Peter
Publication year - 2001
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1560/p2j6-2mn2-0whq-r3bf
Subject(s) - chemistry , nucleophile , bromide , medicinal chemistry , mechanism (biology) , ion , stereochemistry , organic chemistry , catalysis , philosophy , epistemology
Glycosylations using glucosyl bromides and various promoters (Et 4 NBr, HgBr 2 , or AgOTf) were investigated, competitively and kinetically. The reactions were found to be dependent in both glucosyl bromide and nucleophilic concentration, indicating a S N 2‐type rate, determining step. For the AgOTf promoted reaction an ion pair mechanism involving glucosyl triflates is suggested.