Agoston, Károly and Geyer, Armin (2005) Regioselective conversion of the secondary hydroxyl groups of D-glucuronic acid without the requirement of O-protecting groups. CHEMISTRY-A EUROPEAN JOURNAL, 11 (21). pp. 6407-6413. ISSN 0947-6539, 1521-3765
Full text not available from this repository. (Request a copy)Abstract
Trifluoromethanesulfonic acid anhydride (triflic acid anhydride) transforms the bicyclic thiazolidinlactam 1a into the crystalline elimination product 2, in which all four secondary hydroxyl groups of 1a 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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | RESISTANCE REVERSING ACTIVITY; BETA-D-GLUCOSE; BUILDING-BLOCKS; COMBINATORIAL SYNTHESIS; BIOLOGICAL EVALUATION; SMALL MOLECULES; DRUG DISCOVERY; DESIGN; SCAFFOLDS; MIMETICS; carbohydrates; glucose; hapalosin; synthetic methods; thiazolidinlactams |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 26 Apr 2021 05:26 |
| Last Modified: | 26 Apr 2021 05:26 |
| URI: | https://pred.uni-regensburg.de/id/eprint/35524 |
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