title: First example of 5/6-O-linked pseudosaccharides: synthesis of bicyclic nucleosides containing azido or extended carbohydrate moiety.
abstract: Treatment of the d-glucose-derived substrate 1 with sodium hydride in tetrahydrofuran provided 3,6-anhydro monosaccharide 2, along with the 5,6-ether linked pseudodisaccharide 3, and pseudotrisaccharide 4. However, reaction of 1 with sodium ethoxide in ethanol afforded 2 as the sole product, elaborated to the bicyclic azidonucleosides 9 and 16. Acetylated bicyclic nucleosides 17-19 with extended carbohydrate residues have been synthesized from 3.
authors.affiliation: Division of Chemistry, Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Jadavpur, Kolkata 700 032, India.
authors.forename: Joy Krishna
authors.initials: JK
authors.lastname: Maity
authors.forename: Subhranshu
authors.initials: S
authors.lastname: Mukherjee
authors.forename: Michael G B
authors.initials: MG
authors.lastname: Drew
authors.forename: Basudeb
authors.initials: B
authors.lastname: Achari
authors.forename: Sukhendu B
authors.initials: SB
authors.lastname: Mandal
mesh_terms: D001413:Bacillus thuringiensis / Q000378:metabolism; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000737:chemistry*; D018360:Crystallography, X-Ray / Q000379:methods; D004305:Dose-Response Relationship, Drug; D005947:Glucose / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*; D011134:Polysaccharides / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013696:Temperature
chemical_list: D002241:Carbohydrates; D009705:Nucleosides; D011134:Polysaccharides; D005947:Glucose