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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-α-D-galactopyranoside

✍ Scribed by Jingyu Zhang; Xuehui Hou; Hongmin Liu

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
204 KB
Volume
29
Category
Article
ISSN
0256-7660

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✦ Synopsis

Abstract

A novel anhydrogalactosucrose derivative 2′‐methoxyl‐O‐1′,4′:3′,6′‐dianhydro‐β‐D‐fructofuranosyl 3,6‐anhydro‐4‐chloro‐4‐deoxy‐α‐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 ^1^H NMR, ^13^C 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)OC(5)≈C(3′)OC(6′)≈C(1′)OC(4′)>C(3)OC(6)≈C(1)OC(2′)>C(2′)OC(5′).

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