Phenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-b-D-thioglucopyranoside

Phenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-thioglucopyranoside is a sophisticated synthetic thioglycoside derivative characterized by a β-D-glucopyranose core where the hydroxyl groups at positions 4 and 6 are protected by a benzylidene acetal, and the hydroxyl group at position 2 is replaced by a phthalimido group. The anomeric oxygen is substituted by sulfur linked to a phenyl group, creating a thioglycosidic linkage that offers enhanced resistance against hydrolysis. This compound typically appears as a white to off-white crystalline solid with a molecular formula of C27H23NO5S and a molecular weight of about 465.53 g/mol. It is synthesized through a sequence involving selective benzylidene acetal formation, phthalimido substitution, and thioglycosylation with phenyl thiol, followed by purification via chromatography to ensure high purity (≥95%). Analytical characterization involves NMR spectroscopy, mass spectrometry, and chromatographic purity assessments, ensuring low microbial contamination due to synthetic preparation. Storage under cool, dry, and light-protected conditions (2–8 °C) supports a shelf life of 1–2 years. Applications include glycosyl donor roles for stereoselective glycosylation in complex carbohydrate synthesis, glycomimetic development, biochemical probe design, and medicinal chemistry targeting carbohydrate-protein interactions and enzymatic functions.​

IUPAC Name

• Phenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranosi

Appearance

• White to off-white crystalline powder

Source

• Synthesized by benzylidene acetal formation at O4 and O6, phthalimido substitution at C2, and thioglycosylation at anomeric carbon using phenyl thiol
• Purified by column chromatography ensuring chemical purity and batch consistency

Molecular Weight and Structure

• Molecular Formula: C27H23NO5S
• Molecular Weight: 465.53 g/mol
• Structure: β-D-glucopyranose ring with benzylidene protecting group spanning O4 and O6, phthalimido modification at C2, and sulfur linked to phenyl group at anomeric position
• Combines protective groups and thioglycosidic bond for stability and reactivity

Sugar Specificity

• β-Anomeric thioglycoside derivative of 2-deoxy-2-phthalimido-glucopyranose
• Mimics biologically relevant amino sugar structures for glycan synthesis

Biological Activity

• Not intrinsically bioactive but serves as a critical synthetic intermediate
• Used to produce bioactive glycoconjugates and glycomimetics
• Enables biochemical and enzymatic studies involving amino sugar motifs

Purity and Microbial Contamination

• High purity (≥95%) confirmed by NMR and chromatographic methods
• Minimal microbial contamination due to chemical synthesis and purification

Identity and Quality Control

• Verified by 1H/13C NMR, MS, and HPLC purity profiling
• Accompanied by Certificates of Analysis and Safety Data Sheets
• Batch validation via melting point and optical rotation data

Shelf Life and Storage

• Store sealed at 2–8 °C
• Protect from moisture, light, and heat
• Shelf life of 1–2 years under optimal storage conditions

Application

• Used as a glycosyl donor in stereoselective oligosaccharide and glycoconjugate synthesis
• Intermediate in drug design involving amino sugar conjugates
• Applied in enzyme substrate and inhibitor development
• Molecular probe synthesis for carbohydrate recognition studies

Key Characteristics

• Phenyl-substituted thioglycoside of 2-deoxy-2-phthalimido-β-D-glucopyranose with benzylidene protection
• Molecular Weight: 465.53 g/mol
• White crystalline solid with high purity and hydrolytic stability
• Suitable for regio- and stereoselective glycosylation
• Full analytical and quality assurance documentation provided
• Stable under refrigerated, moisture-free storage
• Widely used in glycochemistry and medicinal chemistry research

Citations

• Cymit Química chemical profile​
• PubChem compound data​
• Sigma-Aldrich reagent catalog​
• MedChemExpress glycomimetic intermediates
• PMC biochemical studies
• ChemSpider molecular information​
• Synthose synthetic carbohydrate intermediates
• Patent literature on phthalimido thioglycosides
• Thermo Fisher Scientific reagents
• ScienceDirect reviews on synthetic glycobiology