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Methyl 1,2‐Orthoesters as Useful Glycosyl Donors in Glycosylation Reactions: A Comparison with n ‐Pent‐4‐enyl 1,2‐Orthoesters
Author(s) -
Uriel Clara,
Ventura Juan,
Gómez Ana M.,
López J. Cristóbal,
FraserReid Bert
Publication year - 2012
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.201200089
Subject(s) - chemistry , glycosylation , regioselectivity , monosaccharide , glycosyl , stereochemistry , glycosyl donor , catalysis , organic chemistry , biochemistry
Mannopyranose‐derived methyl 1,2‐orthoacetates (R = Me) and ‐benzoates (R = Ph) can function as glycosyl donors – upon BF 3 · Et 2 O activation in CH 2 Cl 2 – in glycosylation reactions with monosaccharide acceptors to afford disaccharides in good yields. In the process, glycosylation is preferred to acid‐catalyzed rearrangement leading to methyl mannopyranosides. Methyl 1,2‐orthoesters can be also used in regioselective glycosylation protocols with monosaccharide diols, in which they display good regioselectivity.