10.1021/ol101625p.s001
Dennis C. Koester
Dennis C.
Koester
Markus Leibeling
Markus
Leibeling
Roman Neufeld
Roman
Neufeld
Daniel B. Werz
Daniel B.
Werz
A Pd-Catalyzed Approach to (1→6)-Linked <i>C</i>-Glycosides
American Chemical Society
2010
hydride source
hydroxyl group pattern
Approach
DMDO
alkynyl glycosides
hydrogenation
access
method
Epoxidation
assembly
Reinstallation
disaccharide
iodo
reductive epoxide opening
bond
2010-09-03 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/A_Pd_Catalyzed_Approach_to_1_6_Linked_i_C_i_Glycosides/2735923
A flexible and robust method for the assembly of (1→6)-linked <i>C</i>-glycosidic disaccharides is presented. The key reaction is a Pd-catalyzed coupling of 1-iodo- or 1-triflato-glycals with alkynyl glycosides. Reinstallation of the native hydroxyl group pattern is achieved after selective hydrogenation of the triple bond using Raney-nickel. Epoxidation with DMDO and reductive epoxide opening gives access to either the α- or the β-derivative, depending on the hydride source.