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.
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.
Liu
Feng-Wu
FW
School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, PR China. fwliu@zzu.edu.cn
Wang
Zhen-Ji
ZJ
Song
Xiao-Ping
XP
Zhang
Sai-Yang
SY
Liu
Hong-Min
HM
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
D000438:Alcohols; D002241:Carbohydrates; D009595:Nitroparaffins; C014705:nitroethane; D004980:Ethane; D008697:Methane; C008640:nitromethane