title: Facile synthesis of β- and α-arabinofuranosides and application to cell wall motifs of M. tuberculosis.
abstract: Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.
authors: Department of Chemistry, Indian Institute of Science Education and Research , Pune 411 008, India.
authors: Shivaji A
authors: SA
authors: Thadke
authors: Bijoyananda
authors: B
authors: Mishra
authors: Srinivas
authors: S
authors: Hotha
mesh_terms: D001089:Arabinose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D002473:Cell Wall / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006046:Gold; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000737:chemistry* / Q000378:metabolism; D010084:Oxidation-Reduction
chemical_list: D006027:Glycosides; D006046:Gold; D001089:Arabinose