Two halodeoxy sucrose analogues.
At 160 K, the structure of 4-bromo-4-deoxysucrose, C(12)H(21)BrO(10), is very similar to that of sucrose, particularly with respect to the conformation of the glycosidic linkage. As in sucrose, an intramolecular hydrogen bond exists between the glucopyranosyl and the fructofuranosyl rings. Conversely, the structure of 1',6'-dibromo-4-fluoro-4,1',6'-trideoxysucrose monohydrate, C(12)H(19)Br(2)FO(8) x H(2)O, shows large conformational differences when compared with the structures of both sucrose and sucralose. This compound does not exhibit any intramolecular hydrogen bonds. In each compound, a complex series of intermolecular hydrogen bonds link the molecules into an infinite three-dimensional framework. The absolute configuration of each molecule has been determined.
Linden
A
A
Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland. alinden@oci.unizh.ch
Lee
C K
CK
Muhammad Sofian
A S
AS
D018360:Crystallography, X-Ray; D006219:Halogens / Q000737:chemistry; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D013395:Sucrose / Q000031:analogs & derivatives*
C443747:1',6'-dibromo-4-fluoro-4,1',6'-trideoxysucrose monohydrate; D006219:Halogens; D013395:Sucrose