title: Synthesis of L-daunosamine and L-ristosamine glycosides via photoinduced aziridination. Conversion to thioglycosides for use in glycosylation reactions.
abstract: Application of photoinduced acylnitrene aziridination to the syntheses of L-daunosamine and L-ristosamine glycosides is reported. Photoreaction of methyl 4-O-azidocarbonyl-2,3,6-trideoxy-L-hex-2-enopyranosides, followed by aziridine opening, leads to 3-amino-3-N-,4-O-carbonyl-2,3,6-trideoxy precursors to the aminosugar methyl glycosides. Conversion of these precursors to their thioglycoside analogues followed by N-acetylation of the carbamate moiety permits high yielding and, in some cases, stereoselective glycosylations using the 1-benzenesulfinylpiperidine-triflic anhydride activation method developed by Crich and co-workers. Glycosylations involving activation with N-iodosuccinimide and silver triflate were also successful, but the stereoselectivities of these reactions in general were lower.
authors.affiliation: Department of Chemistry, Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
authors.forename: Matthew T
authors.initials: MT
authors.lastname: Mendlik
authors.forename: Peng
authors.initials: P
authors.lastname: Tao
authors.forename: Christopher M
authors.initials: CM
authors.lastname: Hadad
authors.forename: Robert S
authors.initials: RS
authors.lastname: Coleman
authors.forename: Todd L
authors.initials: TL
authors.lastname: Lowary
mesh_terms: D006595:Hexosamines / Q000138:chemical synthesis*
chemical_list: D006595:Hexosamines; C007217:daunosamine