Concise synthesis of a pentasaccharide related to the anti-leishmanial triterpenoid saponin isolated from Maesa balansae
Rajput, VK; Mukhopadhyay, B
| HERO ID | 631978 |
|---|---|
| In Press | No |
| Year | 2008 |
| Title | Concise synthesis of a pentasaccharide related to the anti-leishmanial triterpenoid saponin isolated from Maesa balansae |
| Authors | Rajput, VK; Mukhopadhyay, B |
| Journal | Journal of Organic Chemistry |
| Volume | 73 |
| Issue | 17 |
| Page Numbers | 6924-6927 |
| Abstract | Concise synthesis of the glycone part (a pentasaccharide) of the anti-leishmanial triterpenoid saponin isolated from Maesa balansae is reported. A late-stage TEMPO-mediated oxidation of a primary hydroxyl group to carboxylic acid has been achieved under phase-transfer conditions. Glycosylations were performed either by thioglycoside or glycosyl trichloroacetimidate activation using sulfuric acid immobilized on silica (H2SO4-silica) in conjunction with N-iodosuccinimide and alone, respectively. H2SO4-silica was proved to be a better choice as promoter than conventional Lewis acid promoters such as TfOH or TMSOTf |
| Doi | 10.1021/jo801171f |
| Pmid | 18672936 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |
| Keyword | Acids; analogs & derivatives; Animals; Antiprotozoal Agents; chemical synthesis; chemistry; drug effects; Glycosylation; Leishmania; Mesylates; Models,Chemical; Myrsinaceae; Oligosaccharides; pharmacology; PubMed 07/14/08 to 03/03/09; Saponins; Silicon; Silicon Dioxide; Succinimides; Sulfuric Acids; Thioglycosides; Trichloroacetic Acid; Trimethylsilyl Compounds; Triterpenes |
| Is Qa | No |