A novel glycoside lactone derivative with a 2-C-unsaturated diester substituent.
The title 4,6-O-benzylidene-alpha-D-glucopyranoside (systematic name: methyl 4-methoxy-2-oxo-8-phenyl-1,2,5a,6,9a,9b-hexahydro-4H,8H-7,9-dioxacyclopenta[c]chromene-3-carboxylate), C(18)H(18)O(8), has been synthesized from the reaction of methyl 4,6-O-benzylidene-alpha-D-2-ketoglucopyranoside with diethyl or dimethyl malonate. The compound adopts a chair-chair conformation. The newly formed five-membered ring is fused to the glucopyranoside ring along the C(2)--C(3) bond and is planar with an r.m.s. deviation of 0.0091 A.
Zhang
F
F
Chemistry Department, Zhengzhou University, Zhengzhou 450052, People's Republic of China.
Du
C X
CX
Liu
H M
HM
Zhu
Y
Y
D018360:Crystallography, X-Ray; D006027:Glycosides / Q000737:chemistry*; D006860:Hydrogen Bonding; D007783:Lactones / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009005:Monosaccharides / Q000737:chemistry*
C443746:4,6-O-benzylidene-glucopyranoside; D006027:Glycosides; D007783:Lactones; D009005:Monosaccharides