Comparative X-Ray Single Crystal Study of Acetylated-β-D-Galactopyranosyls Azide and Isothiocyanate

ABSTRACT The structures of two peracetylated β-D-galactopyranosides substituted at the anomeric C atom with either an isothiocyanate or an azide group, have been determined by single crystal X-ray diffraction analysis. The two compounds show very similar molecular conformation, except for the substituent groups at the anomeric C atom and for the acetyl groups of the O6 atoms. They crystallize in different infinite chain-type structures. While the isothiocyanate group extends in a large intermolecular space, the azide group is placed in a more crowded environment.

[1]  H. Parrot-Lopez,et al.  Synthesis of Cyclodextrin Derivatives Carrying Bio-Recognisable Saccharide Antennae , 1997 .

[2]  H. Duddeck,et al.  Synthesis and conformational analysis of plant hormone (auxin) related compound 2-(indol-3-yl) ethyl β-d-galactopyranoside and its 2,3,4,6-tetra-O-acetyl derivative , 1995 .

[3]  W. Saenger,et al.  Geometry of carbon-hydrogen.cntdot..cntdot..cntdot.oxygen hydrogen bonds in carbohydrate crystal structures. Analysis of neutron diffraction data , 1992 .

[4]  Professor Dr. George A. Jeffrey,et al.  Hydrogen Bonding in Biological Structures , 1991, Springer Berlin Heidelberg.

[5]  Owen Johnson,et al.  The development of versions 3 and 4 of the Cambridge Structural Database System , 1991, J. Chem. Inf. Comput. Sci..

[6]  G. A. Jeffrey,et al.  Crystallographic studies of carbohydrates. , 1990, Acta crystallographica. Section B, Structural science.

[7]  T. Srikrishnan,et al.  Crystal Structure of 1,3,4,6-Tetra-O-Acetyl-2-deoxy-2-fluoro-β-D-Galactopyranoside , 1988 .

[8]  H. Kunz.  Synthesis of Glycopeptides, Partial Structures of Biological Recognition Components [New Synthetic Methods (67)] , 1987 .

[9]  M. García-López,et al.  A New Procedure for the Synthesis of Glycosyl Isothiocyanates , 1984 .

[10]  B. Kojić-Prodić,et al.  1,3,4,6‐Tetra‐O‐acetyl‐2‐(N‐acetylacetamido)‐2‐deoxy‐β‐d‐galactopyranose , 1980 .

[11]  H. Paulsen,et al.  Röntgenstrukturanalyse von tri-O-acetyl-β-d-xylopyranosylazid zur Untersuchung des exo-anomeren Effekts der Azidogruppe , 1976 .

[12]  B. Sheldrick.  The crystal structures of the a- and -anomers of D-galactose , 1976 .

[13]  C. Foces-Foces,et al.  Crystal structures of analogues of d‐galactose. II. 2,3,4,6‐Tetra‐O‐acetyl‐1‐cyano‐β‐d‐galactopyranose (CTAG) , 1976 .

[14]  K. Lindberg.  Methyl 6‐O‐acetyl‐β‐d‐galactopyranoside , 1976 .

[15]  A. Neuman,et al.  Structure cristalline du β-d-galactose et de l'α-l-fucose , 1975 .

[16]  F. S. Mathews,et al.  A semi-empirical method of absorption correction , 1968 .

[17]  T. Steiner.  Unrolling the hydrogen bond properties of C–H···O interactions , 1997 .

[18]  R. Faure,et al.  Synthesis and spectroscopic studies of acetylated alkyl 1-azido-D-glucopyranosides , 1993 .

[19]  G. Desiraju,et al.  A crystallographic scale of carbon acidity , 1992 .

[20]  R. Roy,et al.  Phase Transfer Catalysis as a General and Stereoselective Entry into Glycosyl Azides from Glycosyl Halides , 1992 .