title: Efficient synthesis of oligosaccharyl 1,2-O-orthoesters from n-pentenyl glycosides and application to the pentaarabinofuranoside of the mycobacterial cell surface.
abstract: 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.
authors.affiliation: Indian Institute of Science Education & Research, Department of Chemistry, Pune, Maharashtra, India. s.hotha@iiserpune.ac.in.
authors.forename: Shivaji A
authors.initials: SA
authors.lastname: Thadke
authors.forename: Srinivas
authors.initials: S
authors.lastname: Hotha
mesh_terms: D001089:Arabinose / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D008968:Molecular Conformation; D009169:Mycobacterium tuberculosis / Q000737:chemistry* / Q000166:cytology; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013499:Surface Properties
chemical_list: D006027:Glycosides; D009844:Oligosaccharides; D001089:Arabinose