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Catalyzed Acetal Reduction with BH Boranes—1‐ O ‐Alkyl(aryl)alditols, Anhydroalditols, and 1‐ O ‐Alditylalditols from O ‐Glycopyranosides
Author(s) -
Köster Roland,
PenadésUllate Soledad,
Dahlhoff Wilhelm Volker
Publication year - 1985
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198505191
Subject(s) - chemistry , acetal , alkyl , medicinal chemistry , boranes , aryl , stereochemistry , organic chemistry , boron
The conversion of glycosides and disaccharides into alditol derivatives has been accomplished with ethyldiboranes(6) in the presence of 9‐methanesulfonyloxy‐9‐borabicyclo‐[3.3.1]nonane. As example, the per‐ O ‐diethylboryl‐ D ‐galactoside 1 , RBEt 2 , X α H, X β OPh, can be reduced to the 1‐ O ‐phenyl‐ D ‐galactitol derivative 2 , RBEt 2 ; the protective groups can be removed.