Boehlich, Gordon Jacob and Sterzel, Hannes and Rehbein, Julia and Schützenmeister, Nina (2022) Efficient Copper-Catalyzed Highly Stereoselective Synthesis of Unprotected C-Acyl Manno-, Rhamno- and Lyxopyranosides. CHEMISTRY-A EUROPEAN JOURNAL, 28 (71): e202202619. ISSN 0947-6539, 1521-3765
Full text not available from this repository. (Request a copy)Abstract
Due to their high stability towards enzymatic hydrolysis C-acyl glycosidic compounds are useful synthetic intermediates for potential candidates in drug discovery. Syntheses for C-acyl mannosides have remained scarce and usually employ donors obtained from lengthy syntheses. Furthermore, syntheses of unprotected C-acyl mannosides have not been reported so far, due to the incapability of the C-acyl mannoside motif with deprotection conditions for protective groups commonly used in carbohydrate chemistry. Herein, we report an efficient and highly alpha-selective four-step one-pot method for the synthesis of C-acyl alpha-d-manno-, l-rhamno- and d-lyxopyranosides from easily accessible persilylated monosaccharides and dithianes requiring only trace amounts of a copper source as catalyst and explain the crucial role of the catalyst by mechanistic studies. Furthermore, the C-acyl alpha-glycosides were easily isomerized to give rapid access to their beta-anomers.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | MOLECULAR-ORBITAL METHODS; BASIS-SETS; GLYCOSYL; ACCESS; ARYL; CONFORMATION; MANNOPYRANOSIDES; RESIDUE; NICKEL; ACIDS; carbohydrates; C-glycosylation; corey-seebach reaction; copper catalysis; reaction mechanism |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 15 Feb 2024 06:54 |
| Last Modified: | 29 Feb 2024 15:08 |
| URI: | https://pred.uni-regensburg.de/id/eprint/57572 |
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