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Iron(III)‐Triflate‐Catalyzed Multiple Glycosylations with Peracetylated β‐d‐Glucosamine
Author(s) -
Xolin Amandine,
Norsikian Stéphanie,
Boyer FrançoisDidier,
Beau JeanMarie
Publication year - 2016
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.201600457
Subject(s) - chemistry , propargyl , trifluoromethanesulfonate , cycloaddition , catalysis , glycan , microwave chemistry , glycosylation , alkyne , azide , mannose , isatin , combinatorial chemistry , linker , propargyl alcohol , organic chemistry , microwave irradiation , biochemistry , computer science , glycoprotein , operating system
Direct multiple glycosylations of thioaryl and propargyl mannopyranosides with peracetylated β‐ d ‐glucosamine have been carried out using catalytic iron(III) triflate as a promoter in the presence of 2,4,6‐tri‐ tert ‐butylpyrimidine under microwave irradiation. This has led to the one‐step formation of various oligosaccharides with mannose at the branching point. Subsequent direct introduction of a linker through copper‐catalyzed azide–alkyne cycloaddition with the propargyl branched glycan and final deprotection gave rapid access to N ‐glycan mimetics.