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

4-Methylphenyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-galactopyranoside 4-Methylphenyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-galactopyranoside is a complex thioglycoside derivative used in carbohydrate chemistry and glycoconjugate synthesis. This compound features multiple protective groups strategically placed to enable controlled reactivity during oligosaccharide assembly. Structural Features Core structure : β-D-galactopyranoside backbone with a 4-methylphenyl thio-group at the anomeric position (C1). Protective groups : Benzoyl at O-2 for acid-labile protection. Benzyl groups at O-3 and O-4 for stability under basic conditions. 9-Fluorenylmethoxycarbonyl (Fmoc) at O-6, a base-labile protecting group allowing selective deprotection. Synthesis and Applications Synthesis : Typically involves sequential protection steps: Benzoylation of O-2. Benzylation of O-3 and O-4. Fmoc installation at O-6. Thio-glycoside formation via reaction with 4-methylthiophenol. Applications : Key intermediate in synthesizing glycosylated biomolecules. Enables site-specific modifications in glycan assembly due to orthogonal protecting groups. Physicochemical Properties Molecular formula : Likely C₅₀H₅₀O₈S (estimated based on similar structures). Appearance : White crystalline solid. Solubility : Soluble in DMSO, DCM, and DMF. Storage : Recommended at -20°C for long-term stability. Safety and Handling Classified as non-hazardous under GHS guidelines. Standard laboratory precautions apply for organic compounds (gloves, ventilation). This compound’s design highlights the precision required in glycan engineering, balancing protective group compatibility and reactivity for targeted biochemical applications. Citations: https://glycomindsynth.com/product_detail/517/Monosaccharide https://www.pharmaffiliates.com/en/2088577-19-7-4-methylphenyl-2-o-benzoyl-3-6-di-o-benzyl-4-o-9-fluorenylmethoxycarbonyl-1-thio-beta-d-galactopyranoside-pa270026106.html https://www.chemicalbook.com/ProdSupplierGWCB29036383_EN.htm https://www.bocsci.com/product/4-methylphenyl-2-o-benzoyl-3-6-di-o-benzyl-4-cas-2088577-19-7-339099.html https://pubchem.ncbi.nlm.nih.gov/compound/1326804-93-6 https://www.chemicalbook.com/ProductChemicalPropertiesCB09036329_EN.htm https://synthose.com/products/ML822 https://www.pharmaffiliates.com/en/parentapi/miscellaneous-impurities?page=289 https://synthose.com/products/MG340