Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides
| Autor: | K Singh Amrendra, Banik Bimal, Naresh Yadav Ram |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
animal structures 010405 organic chemistry Chemistry Organic Chemistry One-pot synthesis Glycoside macromolecular substances 010402 general chemistry 01 natural sciences 0104 chemical sciences Catalysis carbohydrates (lipids) Acetylation Hydrogenolysis Organic chemistry lipids (amino acids peptides and proteins) Indium bromide |
| Zdroj: | Current Organic Chemistry. 24:900-908 |
| ISSN: | 1385-2728 |
| DOI: | 10.2174/1385272824999200407093625 |
| Popis: | Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest. |
| Databáze: | OpenAIRE |
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