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The Heyns Rearrangement Revisited: An Exceptionally Simple Two‐Step Chemical Synthesis of D ‐Lactosamine from Lactulose
Author(s) -
Wrodnigg Tanja M.,
Stütz Arnold E.
Publication year - 1999
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/(sici)1521-3773(19990315)38:6<827::aid-anie827>3.0.co;2-n
Subject(s) - chemistry , lactulose , glucosamine , glycosyl , ammonia , fructose , residue (chemistry) , stereochemistry , organic chemistry , biochemistry
Disaccharides containing D ‐glucosamine at the reducing end can be conveniently synthesized in good yields from O‐glycosylated D ‐fructoses by the title reaction [Eq. (a)]. With all the disaccharides investigated, the method proceeded—presumably because of the pronounced destabilizing interactions of the glycosyl residue at O‐4 with the other polar groups—considerably more efficiently than with unsubstituted D ‐fructose, whose reaction with ammonia to give D ‐glucosamine was described by Heyns and Koch in the 1950s.