A facile approach to anhydrogalactosucrose derivatives from chlorinated sucrose.
Three new anhydrosucrose derivatives: 1,4:3,6-dianhydro-beta-D-fructofuranosyl 4-chloro-4-deoxy-alpha-D-galactopyranoside (4), 1,4:3,6-dianhydro-beta-D-fructofuranosyl 3,6-anhydro-4-chloro-4-deoxy-alpha-D-galactopyranoside (6) and 1,6-dichloro-1,6-dideoxy-beta-D-fructofuranosyl-3,6-anhydro-4-chloro-4-deoxy-alpha-D-galactopyranoside (8) were prepared from chlorinated sucrose. The structures of these anhydrides were confirmed by their (1)H and (13)C NMR spectra, ESIMS and elemental analysis. The crystal structures of 6 and the acetate of 4 (5) are presented. The relative reactivity of the chloromethyl groups towards S(N)2 reactions in 1,6-dichloro-1,6-dideoxy-beta-d-fructofuranosyl 4,6-dichloro-4,6-dideoxy-alpha-D-galactopyranoside was found to be in order 6>6'>1'.
Liu
Feng-Wu
FW
Department of Chemistry, Zhengzhou University, Zhengzhou 450052, PR China.
Liu
Hong-Min
HM
Ke
Yu
Y
Zhang
Jingyu
J
D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013395:Sucrose / Q000031:analogs & derivatives* / Q000737:chemistry; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D014312:Trisaccharides; D013395:Sucrose; C081752:galactosucrose