Regioselective conversion of the secondary hydroxyl groups of D-glucuronic acid without the requirement of O-protecting groups

Agoston, K.ár.; Geyer, A.

Chemistry 11(21): 6407-6413

2005


ISSN/ISBN: 0947-6539
PMID: 16094680
DOI: 10.1002/chem.200500515
Accession: 050148654

Download citation:  
Text
  |  
BibTeX
  |  
RIS

Article/Abstract emailed within 0-6 h
Payments are secure & encrypted
Powered by Stripe
Powered by PayPal

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.

Regioselective conversion of the secondary hydroxyl groups of D-glucuronic acid without the requirement of O-protecting groups