title: Allyloxy and propargyloxy group migration: role of remote group participation in the synthesis of 5-C-nucleosides and other sugar derivatives.
abstract: In 1-deoxy-xylofuranose derivatives possessing a good leaving group at 2-C, participation of allyloxy and propargyloxy substituents at 5-C results in loss of the 2-C substituent and attack of various nucleophiles at 5-C of the oxonium intermediate. Such participation of a benzyloxy or crotyloxy group leads to dioxabicyclo[2.2.1]heptane rings.
authors.affiliation: Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Jadavpur, Kolkata 700 032, India.
authors.forename: Subhrangshu
authors.initials: S
authors.lastname: Mukherjee
authors.forename: Prabhash N
authors.initials: PN
authors.lastname: Tripathi
authors.forename: Sukhendu B
authors.initials: SB
authors.lastname: Mandal
mesh_terms: D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D014994:Xylose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009705:Nucleosides; D014994:Xylose