Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 17, Pages 6572-6581Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201406589
Keywords
aglycone delivery; carbohydrates; glycosylation; leaving group; stereocontrol
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Funding
- NSF [CHE-1058112, CHE-0959360]
- Mizutani Foundation for Glycosciences [130057]
- UM-St. Louis Graduate School
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1058112] Funding Source: National Science Foundation
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Described herein is the expansion of the picoloyl protecting-group assisted H-bond mediated aglycone delivery (HAD) method recently introduced by our laboratory. At first it was noticed that high -stereoselectivity is only obtained with S-ethyl glycosyl donors and only in the presence of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST), in high dilution, and low temperature. Combining the mechanistic studies of the HAD reaction and bromine-promoted glycosylations allowed a very effective method to be devised that allows for highly stereoselective -glycosidation of practically all common leaving groups (S-phenyl, S-tolyl, S/O-imidates) at regular concentrations and ambient temperature.
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