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Development of Ketoside‐Type Analogues of Trehalose by Using α‐Stereoselective O‐Glycosidation of Ketose
Author(s) -
Namme Rie,
Mitsugi Takashi,
Takahashi Hideyo,
Ikegami Shiro
Publication year - 2007
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.200700145
Subject(s) - chemistry , hydrogenolysis , stereoselectivity , trehalose , trimethylsilyl trifluoromethanesulfonate , ketose , trimethylsilyl , trifluoromethanesulfonate , aldose , stereochemistry , trisaccharide , organic chemistry , catalysis , glycoside
The stereoselective synthesis of ketoside‐type analogues of trehalose is described. O‐Glycosidation of hept‐2‐ulopyranose with trimethylsilyl α‐pyranoside promoted by trimethylsilyl trifluoromethanesulfonate afforded α‐ketopyranosyl α‐aldopyranosides exclusively. α‐Ketopyranosyl β‐aldooyranosides and α‐ketopyranosyl α‐ketopyranosides were also synthesized in a similar manner. The benzyl protecting groups of the hydroxy moieties were removed by hydrogenolysis to afford fully deprotected trehalose analogues.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)