3,4-Dicyano-phenyl 2,3,4,6-tetra-O-acetyl-α-d-glucopyran-oside

Area of Science:

• Organic Chemistry
• Crystallography
• Carbohydrate Chemistry

Background:

• Phthalonitrile derivatives are important intermediates in organic synthesis.
• Glycosidation is a key reaction for forming glycosidic bonds.
• Understanding molecular structure and interactions is crucial in chemistry.

Purpose of the Study:

• To synthesize a novel C(22)H(22)N(2)O(10) compound.
• To characterize the structure and absolute configuration of the synthesized molecule.
• To investigate the crystal packing and intermolecular interactions.

Main Methods:

• Glycosidation reaction via nitrite displacement on substituted nitro-phthalonitrile.
• Determination of absolute configuration using d-glucose as a starting material.
• Analysis of crystal structure and hydrogen bonding interactions.

Main Results:

• Successful synthesis of the title compound C(22)H(22)N(2)O(10).
• The molecule comprises a benzene ring, two nitrile groups, and an acetyl-protected d-glucose fragment in a chair conformation.
• The exclusive presence of the alpha-anomer with all protected sugar substituents in equatorial positions was confirmed.
• Crystal packing is stabilized by C-H⋯O and C-H⋯N hydrogen bonds.

Conclusions:

• The study successfully synthesized and characterized a novel glycosylated phthalonitrile derivative.
• The stereochemistry and conformation of the d-glucose moiety were elucidated.
• Intermolecular hydrogen bonding plays a significant role in the crystal structure stabilization.