title: The Henry reaction of (1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-1,4:3,6-dianhydro-D-fructose 5,5'-dinitrate. Different reactive features of nitromethane to nitroethane.
abstract: Henry reactions of a novel higher sugar derivative, (1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-1,4:3,6-dianhydro-D-fructose 5,5'-dinitrate (Alternate nomenclature: (1R)-(isomannid-2-yl)-1,4:3,6-dianhydro-D-fructose 5,5'-dinitrate), with nitromethane and nitroethane were studied. The kinetic and thermodynamic reactions with nitromethane under different conditions were carried out to afford (2S)- and (2R)-beta-nitroalcohols, respectively. But when using nitroethane the reaction gave a (2S)-beta-nitroalcohol with an inverted configuration at vicinal carbon C-1. Two stereogenic centers were generated, and one was altered in the reaction.
authors.affiliation: School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, PR China. fwliu@zzu.edu.cn
authors.forename: Feng-Wu
authors.initials: FW
authors.lastname: Liu
authors.forename: Zhen-Ji
authors.initials: ZJ
authors.lastname: Wang
authors.forename: Xiao-Ping
authors.initials: XP
authors.lastname: Song
authors.forename: Sai-Yang
authors.initials: SY
authors.lastname: Zhang
authors.forename: Hong-Min
authors.initials: HM
authors.lastname: Liu
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis; D002241:Carbohydrates / Q000737:chemistry*; D004980:Ethane / Q000031:analogs & derivatives* / Q000737:chemistry; D007700:Kinetics; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D009595:Nitroparaffins / Q000737:chemistry*; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D000438:Alcohols; D002241:Carbohydrates; D009595:Nitroparaffins; C014705:nitroethane; D004980:Ethane; D008697:Methane; C008640:nitromethane