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Regioselective Conversion of the Secondary Hydroxyl Groups of D ‐Glucuronic Acid without the Requirement of O ‐Protecting Groups
Author(s) -
Ágoston Károly,
Geyer Armin
Publication year - 2005
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.200500515
Subject(s) - chemistry , glucuronic acid , regioselectivity , nucleophile , protecting group , stereoselectivity , triflic acid , organic chemistry , combinatorial chemistry , catalysis , polysaccharide , alkyl
Abstract Trifluoromethanesulfonic acid anhydride (triflic acid anhydride) transforms the bicyclic thiazolidinlactam 1 a into the crystalline elimination product 2 , in which all four secondary hydroxyl groups of 1 a are differently functionalized. Compound 2 can then add nucleophiles with high chemo‐ and stereoselectivity. Altogether, the four secondary hydroxyl groups of D ‐glucuronic acid are selectively transformed without the need for any O ‐protecting groups. Minimizing the number of O ‐protecting groups is a prerequisite for the use of sugar scaffolds in molecular libraries. The hapalosin analogues 15 , 16 , 19 , and 22 outline the strategy towards O ‐diversified glucose derivatives.