Novel synthesis of methyl 4,6-O-benzylidenespiro[2-deoxy-alpha-D-arabino-hexopyranoside-2,2'-imidazolidine] and its homologue and sugar-gamma-butyrolactam derivatives from methyl 4,6-O-benzylidene-alpha-D-arabino-hexopyranosid-2-ulose.
Novel methyl 4,6-O-benzylidenespiro[2-deoxy-alpha-D-arabino-hexopyranoside-2,2'-imidazolidine] and its homologue methyl 4,6-O-benzylidene-3',4',5',6'-tetrahydro-1'H-spiro[2-deoxy-alpha-D-arabino-hexopyranoside-2,2'-pyrimidine] have been synthesized in good yields by reaction of methyl 4,6-O-benzylidene-alpha-D-arabino-hexopyranosid-2-ulose with 1,2-diaminoethane and 1,3-diaminopropane. The results are completely different from the reaction with arylamines or alkylamines. One-pot synthesis of novel (E)-methyl 4-[hydroxy (methoxy)methylene]-5-oxo-1-alkyl-(4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranosido)[3,2-b]pyrrolidines has been achieved by the reaction of alkylamines with the butenolide-containing sugar, derived from the aldol condensation of methyl 4,6-O-benzylidene-alpha-D-arabino-hexopyranosid-2-ulose with diethyl malonate. These sugar-gamma-butyrolactam derivatives are potential GABA receptor ligands.
Zhang
Fuyi
F
Chemistry Department, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, PR China. zhangfy@zzu.edu.cn
Liu
Hong
H
Li
Yong-Feng
YF
Liu
Hong-Min
HM
D048289:Imidazolidines / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000737:chemistry*; D012266:Ribose / Q000031:analogs & derivatives* / Q000737:chemistry*
D048289:Imidazolidines; D011083:Polycyclic Compounds; D012266:Ribose