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l ‐Rhamnosylation: The Solvent is the Solution
Author(s) -
Elferink Hidde,
Pedersen Christian Marcus
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601355
Subject(s) - chemistry , selectivity , nitrile , anomer , glycosylation , solvent , reactivity (psychology) , catalysis , solvent effects , organic chemistry , combinatorial chemistry , biochemistry , medicine , alternative medicine , pathology
Herein we present a systematic study of l ‐rhamnosylation. The influence of protective groups, reactivity, solvents and glycosylation method, i.e. catalytic versus promoted glycosylation, are studied. It was found that the selectivity can be controlled to a large extend, by varying these parameters and hence the same donor can give both anomers. A reversal of the influence of the participating solvents is observed, and hence ethereal solvents increase the β selectivity, whereas nitrile solvents give almost exclusive α‐selectively.