title: Stable Alkynyl Glycosyl Carbonates: Catalytic Anomeric Activation and Synthesis of a Tridecasaccharide Reminiscent of Mycobacterium tuberculosis Cell Wall Lipoarabinomannan.
abstract: Oligosaccharide synthesis is still a challenging task despite the advent of modern glycosidation techniques. Herein, alkynyl glycosyl carbonates are shown to be stable glycosyl donors that can be activated catalytically by gold and silver salts at 25 °C in just 15 min to produce glycosides in excellent yields. Benzoyl glycosyl carbonate donors are solid compounds with a long shelf life. This operationally simple protocol was found to be highly efficient for the synthesis of nucleosides, amino acids, and phenolic and azido glycoconjugates. Repeated use of the carbonate glycosidation method enabled the highly convergent synthesis of tridecaarabinomannan in a rapid manner.
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pune, India.
authors.forename: Bijoyananda
authors.initials: B
authors.lastname: Mishra
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pune, India.
authors.forename: Mahesh
authors.initials: M
authors.lastname: Neralkar
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pune, India. s.hotha@iiserpune.ac.in.
authors.forename: Srinivas
authors.initials: S
authors.lastname: Hotha
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry; D002254:Carbonates / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D002473:Cell Wall / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006046:Gold / Q000737:chemistry; D009169:Mycobacterium tuberculosis / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D002254:Carbonates; D006027:Glycosides; D009844:Oligosaccharides; D006046:Gold
keywords: carbonates; glycoconjugates; glycosidation; gold catalysis; oligosaccharides