Stereospecific synthesis of aldoses based on the epoxide-opening reaction with double inversion of the configuration.
A new synthetic methodology for aldoses and aldonitols was developed in which two stereospecific epoxide-opening reactions with double inversion of the configuration, i.e., the ring-opening reaction of epoxy sulfides with phenylboronic acid and the stereospecific interconversion of trans- and cis-epoxy sulfides, were designed as the key steps. The synthetic potential of the new methodology was exemplified by the highly stereoselective synthesis of two pentose-derived sugars, arabitol and adonitol (ribitol).
Hirai
Atsushi
A
Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo, Japan.
Tonooka
Terumichi
T
Tanino
Keiji
K
Miyashita
Masaaki
M
D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D002241:Carbohydrates; D004852:Epoxy Compounds; D007202:Indicators and Reagents