Crystal Research and Technology
Cryst. Res. Technol. 41, 836 (2006) - Abstract -

Structural studies of crystalline oligosaccharides VI: Crystal structure and conformation of benzyl-4,6-O-benzylidene-3-O-benzoyl-β-D-galactoside

Ren Shen and Thamarapu Srikrishnan

Department of Cancer Biology, Roswell Park Cancer Institute, Buffalo, New York 14263, USA

Keywords x-ray structure, sugar, monsaccharides, galactoside conformation
PACS 61.66.Hq
DOI 10.1002/crat.200510679

Monsaccharides are the building blocks of polysaccharides and hence are the simplest sugar molecules to study the conformation and molecular structures of sugars. Benzyl-4,6-O-benzylidene-3-O-benzoyl-β-D-galactoside is a key intermediate in the synthesis of polysaccharides. Crystal structural investigation of the title compound was undertaken to establish their chemical structure as well as to study their solid state conformation. Crystals of the title compound, obtained from water/methanol, are orthorhombic, space group P212121, with cell dimensions a=11.290 (4), b=9.941 (1), c= 21.442(2)Å, V= 2406Å3, Z=4, Dobs = 1.42 gm/cm3, Dcalc = 1.423 g/cm3, 2886 reflections were collected on a CAD-4 diffractometer. The structure was solved by direct methods and refined to a final reliability index of 4.7%. The galactoside sugar has the chair conformation with C2’ and C5’ deviating from the mean plane of the other atoms of the sugar. The 4,6-O-benzylidene ring also has a chair conformation with the benzoyl group proximal to O6’. The crystal structure is stabilized by O-H…O hydrogen bonds involving O2’ as donor and three C-H…O hydrogen bond interactions.





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