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Deoxygenative Olefination Reaction as the Key Step in the Syntheses of Deoxy and Iminosugars
Author(s) -
Chang Hsu Yung,
Hwu Jih Ru
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201201060
Subject(s) - iminosugar , pentose , chemistry , disaccharide , key (lock) , computer science , combinatorial chemistry , organic chemistry , computer security , fermentation , enzyme
Just a spoonful of sugar! A new synthetic strategy involving the use of a deoxygenative olefination reaction as the key step was developed for the preparation of deoxy and iminosugars in their optically active form (see scheme). This strategy has been proven successful by the use of a pentose, hexose, heptose, and disaccharide as the starting materials. Furthermore, it was applied in a formal total synthesis of iminosugar (−)‐1‐deoxy‐ L ‐fuconojirimycin, which can inhibit α‐ L ‐fucosidase.