Stereoselective synthesis of methyl 4,6-O-benzylidene-2-C-methoxycarbonylmethyl-alpha-D-ribo-hexopyranosid-3-ulose, and its X-ray crystallographic analysis.
Methyl 4,6-O-benzylidene-2-C-methoxycarbonylmethyl-alpha-D-ribo-hexopyranosid-3-ulose has been stereoselectively synthesized in 65% yield by reaction of methyl 4,6-O-benzylidene-alpha-D-arabino-hexopyranosid-2-ulose with diethyl malonate. X-ray crystallographic structure analysis reveals that the chain-branch and the OH group are bonded to C-2 in axial and equatorial positions, respectively. The molecules in the crystal lattice are stacked along a one-dimensional chain, with intermolecular hydrogen bonds between O-8 of one molecule and 2-OH of the next as well as intramolecular hydrogen bonds between O-3 and 2-OH. All phenyl groups are parallel as well as the planes of sugar rings in the molecular columnar stacking.
Liu
H M
HM
Department of Chemistry, Zhengzhou University, 450052, Zhengzhou, China. liuhm@public.zz.ha.cn
Zhang
F
F
Zhang
J
J
D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray / Q000379:methods; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012266:Ribose / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C438447:Methyl 4,6-O-benzylidene-2-C-methoxycarbonylmethyl-ribo-hexopyranosid-3-ulose; D011083:Polycyclic Compounds; D012266:Ribose