Efficient synthesis of oligosaccharyl 1,2-O-orthoesters from n-pentenyl glycosides and application to the pentaarabinofuranoside of the mycobacterial cell surface
| Autor: | Srinivas Hotha, Shivaji A. Thadke |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
chemistry.chemical_classification
biology Surface Properties Stereochemistry Organic Chemistry Molecular Conformation Oligosaccharides Glycoside Mycobacterium tuberculosis Oligosaccharide biology.organism_classification Arabinose Biochemistry Mycobacterial cell chemistry.chemical_compound chemistry Glycosyl Glycosides Physical and Theoretical Chemistry Glycosyl donor |
| Zdroj: | Org. Biomol. Chem.. 12:9914-9920 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c4ob01395f |
| Popis: | Complex oligosaccharide syntheses employ the use of more than one glycosyl donor and hence, methods for the interconversion of glycosyl donors are highly valuable for the overall synthesis plan. Herein, n-pentenyl glycosides are efficiently converted to glycosyl 1,2-O-orthoesters in the presence of both acid and base sensitive functional groups. The identified protocol was found to be suitable for the synthesis of trisaccharyl and tetrasaccharyl 1,2-O-orthoester as well. Furthermore, an iterative synthesis of pentaarabinofuranoside present on the Mycobacterium tuberculosis cell surface was accomplished using this method. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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