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Regioselective and 1,2‐ cis ‐α‐Stereoselective Glycosylation Utilizing Glycosyl‐Acceptor‐Derived Boronic Ester Catalyst
Author(s) -
Nakagawa Akira,
Tanaka Masamichi,
Hanamura Shun,
Takahashi Daisuke,
Toshima Kazunobu
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201504182
Subject(s) - regioselectivity , stereoselectivity , glycosyl , glycosylation , chemistry , glycosyl donor , catalysis , diol , acceptor , glycoside , stereochemistry , organic chemistry , combinatorial chemistry , biochemistry , physics , condensed matter physics
Regioselective and 1,2‐ cis ‐α‐stereoselective glycosylations using 1α,2α‐anhydro glycosyl donors and diol glycosyl acceptors in the presence of a glycosyl‐acceptor‐derived boronic ester catalyst. The reactions proceed smoothly to give the corresponding 1,2‐ cis ‐α‐glycosides with high stereo‐ and regioselectivities in high yields without any further additives under mild reaction conditions. In addition, the present glycosylation method was successfully applied to the synthesis of an isoflavone glycoside.