4-Methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-galactopyranoside

4-Methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-galactopyranoside 4-Methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-galactopyranoside is a synthetic thioglycoside derivative designed for controlled reactivity in carbohydrate chemistry. Its structure features a β-D-galactopyranoside backbone with strategically placed protective groups to enable selective deprotection during oligosaccharide synthesis. Structural Characteristics Core scaffold : β-D-galactopyranoside with a 4-methylphenyl thio-group at the anomeric position (C1). Protective group arrangement : Benzoyl at O-2 (acid-sensitive protection). Benzyl groups at O-4 and O-6 (stable under basic conditions). 9-Fluorenylmethoxycarbonyl (Fmoc) at O-3 (base-labile, allowing orthogonal deprotection). Applications Acts as a glycosidase inhibitor , making it valuable for studying metabolic disorders like diabetes and cancer. Used in glycoconjugate synthesis for site-specific modifications in glycan assembly. Physicochemical Properties Molecular formula : Estimated as C₅₀H₅₀O₈S (based on substituent analysis). Appearance : Likely a white crystalline solid (similar to analogs in search results). Solubility : Compatible with polar aprotic solvents like DMSO, DMF, or DCM. Synthesis Strategy Typical steps include: Sequential installation of benzyl, benzoyl, and Fmoc groups via selective protection reactions. Thio-glycoside formation using 4-methylthiophenol. Safety and Handling Classified as non-hazardous under standard GHS guidelines. Recommended storage at 0–8°C for stability. This compound exemplifies the precision of modern glycosylation strategies, balancing protective group orthogonality and reactivity for biomedical research applications. Citations: https://glycomindsynth.com/product_detail/517/Monosaccharide https://www.chemicalbook.com/ProdSupplierGWCB29036383_EN.htm https://synthose.com/products/ML822 https://www.sigmaaldrich.com/FR/fr/search/4-methoxy-benzyl-isocyanate?focus=papers&page=1&perpage=30&sort=relevance&term=4-methoxy+benzyl+isocyanate&type=citation_search https://synthose.com/products/MG340 https://www.bocsci.com/product/4-methylphenyl-2-o-benzoyl-3-4-di-o-benzyl-6-o-9-fluorenylmethoxycarbonyl-339431.html https://pubchem.ncbi.nlm.nih.gov/compound/72981508 https://labshake.com/product/399e6a13-22b5-482b-aa76-bac0621fa7db/-4-Methylphenyl-2-O-benzoyl-4-6-di-O-benzyl-3-O--9-fluorenylmethoxycarbonyl--1-thio-%CE%B2-D-galactopyranoside