A facile approach to anhydrogalacto sucrose derivatives from chlorinated sucrose

作者：Liu FW; Liu HM^*; Ke Y; Zhang JY

来源：Carbohydrate Research, 2004, 339(16): 2651-2656.

DOI：10.1016/j.carres.2004.09.013

• anhydrosucrose
• chlorinated sucrose
• x-ray analysis
• relative reactivity

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 H-1 and C-13 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'.

• 出版日期2004-11-15
• 单位郑州大学