Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 28, Pages 8041-8044Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201600142
Keywords
carbohydrates; glycosylation; organocatalysis; stereoselectivity; urea
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Funding
- Ministry of Science and Technology of China [2012CB822100, 2013CB910700]
- National Natural Science Foundation of China [21232002, 21572012]
- Beijing Natural Science Foundation [2142015]
- Beijing Higher Education Young Elite Teacher Project [YETP0063]
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A stereoselective Koenigs-Knorr glycosylation reaction under the catalysis of urea is described. This method is characterized by urea-mediated hydrogen-bond activation and subsequent glycosylation with glycosyl chlorides or bromides. Excellent yields and high anomeric selectivity can be achieved in most cases. Moreover, the low alpha-stereoselectivity of glycosylations observed when using perbenzylated glucosyl donors can be greatly improved by the addition of tri-(2,4,6-trimethoxyphenyl) phosphine (TTMPP).
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