Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 12, Issue 48, Pages 9914-9920Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob01395f
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- CSIR New Delhi
- DST New Delhi
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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.
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