Synthesis, Crystal Structure and Hydrolysis of a Novel Anhydrogalactosucrose: 2′-Methoxyl-O-1′,4′:3′,6′-dianhydro-β-D-fructofuranosyl 3,6-anhydro-4-chloro-4-deoxy--D-galactopyranoside

摘要

A novel anhydrogalactosucrose derivative 2′-methoxyl-O-1′,4′:3′,6′-dianhydro-β-D-fructofuranosyl 3,6-anhydro-4-chloro-4-deoxy--D-galactopyranoside (4) was prepared from 3,6:1′,4′:3′,6′-trianhydro-4-chloro-4-deoxy-galactosucrose (3) via a facile method and characterized by 1H NMR, 13C NMR and 2D NMR spectra. The single crystal X-ray diffraction analysis shows that the title molecule forms a two thee-dimensional network structure by two kinds of hydrogen bond interactions [O(2)H(2)···O(7), O(5)H(5)···O(8)]. Its stability was investigated by acid hydrolysis reaction treated with sulfuric acid, together with the formation of 1,6-Di-O-methoxy-4-chloro-4-deoxy-β-D-galactopyranose (5) and 2,2-Di-C-methoxy-1,4:3,6-dianhydromannitol (6). According to the result, the relative stability of the ether bonds in the structure is in the order: C(1)OC(5)≈C(3′)OC(6′)≈C(1′)OC(4′)>C(3)OC(6)≈C(1)OC(2′)>C(2′)OC(5′).