title: Photochemical conversion of the o-nitrobenzyl-C-glucoside to a sugar lactone.
abstract: A new family of activated glycosidic compounds has been designed and synthesized: (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-nitrophenylmethane (1). It is stable in conditions commonly used for synthesis, and it can be converted to a sugar lactone derivative merely by photoirradiation (λ=365 nm): 2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone (2). A mechanism for the reaction is proposed. The photochemical conversion of 1 in the presence of methanol has also been demonstrated, giving rise to methyl 2,3,4,6-tetra-O-acetyl-D-gluconate (3).
authors: Division of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Chiba 263-8522, Japan. kohri@faculty.chiba-u.jp
authors: Michinari
authors: M
authors: Kohri
authors: Takuma
authors: T
authors: Kimura
authors: Yoshihiro
authors: Y
authors: Shinoda
authors: Tatsuo
authors: T
authors: Taniguchi
authors: Takayuki
authors: T
authors: Nakahira
mesh_terms: D005960:Glucosides / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D010777:Photochemistry; D014466:Ultraviolet Rays
chemical_list: D005960:Glucosides; D007783:Lactones