Phenyl 2-deoxy-2-phthalimido-β-D-thioglucopyranoside

Phenyl 2-deoxy-2-phthalimido-β-D-thioglucopyranoside is a chemically synthesized thioglycoside derivative of β-D-glucopyranose with an important modification at the C2 position where a phthalimido group replaces the hydroxyl group, and the anomeric oxygen is substituted by sulfur linked to a phenyl group. This compound combines the structural features of a thioglycoside and a protected amino sugar, yielding enhanced stability and unique reactivity useful in carbohydrate chemistry, especially in the synthesis of complex glycoconjugates and glycomimetics. It appears as a white to off-white crystalline solid with a molecular formula C21H19NO4S and a molecular weight of approximately 381.44 g/mol. Synthesized through the thiolysis of protected β-D-glucopyranosyl intermediates incorporating the phthalimido group, the compound is purified by chromatographic techniques ensuring high purity (≥95%). Analytical characterization employing NMR spectroscopy, mass spectrometry, and chromatographic methods confirms identity and purity, with microbial contamination minimized due to its synthetic nature. Optimal storage involves sealed containers at 2–8 °C protected from moisture and light to maintain stability and a shelf life of 1–2 years. Applications include glycosyl donor roles in stereoselective synthesis, amino sugar conjugate development, pharmaceutical intermediate manufacture, and molecular probe design in glycoscience research.

IUPAC Name

• Phenyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Appearance

• White to off-white crystalline powder

Source

• Synthesized by thiolysis of protected β-D-glucopyranosyl intermediates with phenyl thiol, incorporating phthalimido protection at C2
• Purified via column chromatography ensuring chemical purity and homogeneity

Molecular Weight and Structure

• Molecular Formula: C21H19NO4S
• Molecular Weight: 381.44 g/mol
• Structure: β-D-glucopyranose ring with sulfur at anomeric carbon bonded to phenyl group, and phthalimido substituent at C2
• Features a protected amino sugar thioglycoside with enhanced synthetic utility

Sugar Specificity

• β-Anomer of 2-deoxy-2-phthalimido-glucopyranoside
• Maintains natural stereochemistry useful for biological mimicry and synthetic elaboration

Biological Activity

• Not directly biologically active
• Serves as synthetic intermediate and substrate mimic in amino sugar and glycoconjugate synthesis
• Supports medicinal chemistry aiming at glycan-like drug design

Purity and Microbial Contamination

• Purity >95% verified by NMR and chromatographic methods
• Maintained free of microbial contamination through synthetic preparation

Identity and Quality Control

• Verified by 1H and 13C NMR, MS, and HPLC purity assays
• Supplied with detailed Certificates of Analysis and Safety Data Sheets
• Includes melting point and optical rotation data for batch consistency

Shelf Life and Storage

• Store in sealed containers at 2–8 °C
• Protect from moisture, light, and heat exposure
• Stable with typical shelf life of 1–2 years

Application

• Used as a thioglycosyl donor in stereoselective oligosaccharide syntheses
• Intermediate in synthesis of amino sugar-containing glycoconjugates and glycomimetics
• Enzyme substrate analogue for glycosyltransferases and glycosidases
• Molecular probe precursor for carbohydrate-binding studies and drug development

Key Characteristics

• Thioglycoside of β-D-glucopyranose with C2 phthalimido protection and phenyl group at anomeric carbon
• Molecular weight: 381.44 g/mol
• White crystalline powder with high purity and hydrolytic stability
• Enables regio- and stereoselective glycosylation reactions
• Rigorous analytic characterization ensures quality and reproducibility
• Suitable for long-term storage at refrigerated conditions
• Widely used in synthetic glycochemistry and medicinal chemistry research

Citations

• Cymit Química product data​
• PubChem molecular profile​
• Sigma-Aldrich chemical catalog​
• MedChemExpress carbohydrate intermediates
• PMC enzymology research articles
• ChemSpider chemical information​
• Synthose synthetic glycoside intermediates
• Patent literature on phthalimido thioglycosides
• Thermo Fisher Scientific reagents
• ScienceDirect reviews on synthetic glycobiology