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

4-Methylphenyl 2,3-di-O-benzoyl-4-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-glucopyranoside 4-Methylphenyl 2,3-di-O-benzoyl-4-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-glucopyranoside is a synthetically modified thioglycoside derivative designed for controlled glycosylation reactions in carbohydrate chemistry. This compound features a glucose backbone (β-D-glucopyranoside) with multiple protective groups strategically placed to enable selective reactivity during oligosaccharide synthesis. Structural Features Core structure : A β-D-glucopyranose ring with a sulfur atom replacing the anomeric oxygen, forming a 1-thio linkage to a 4-methylphenyl group. Protective groups : 2- and 3-positions : Benzoyl esters (electron-withdrawing groups that stabilize against acid hydrolysis) 4-position : Benzyl ether (acid-stable, removable via hydrogenolysis) 6-position : 9-Fluorenylmethoxycarbonyl (Fmoc) group - a base-labile protecting group allowing selective deprotection under mild piperidine treatment Key Properties Property Description Molecular Formula C₄₂H₃₈O₇S Molecular Weight 686.81 g/mol Physical Form White crystalline solid Stability Stable under acidic conditions due to benzoyl/benzyl groups Deprotection Specificity Fmoc at C6 can be selectively removed without affecting other protections Synthetic Utility Glycosyl donor : The thioglycoside moiety acts as a leaving group, enabling glycosidic bond formation under thiophilic activation (e.g., NIS/TfOH). Orthogonal protection : Combination of benzoyl (acid-stable), benzyl (hydrogenolysis-sensitive), and Fmoc (base-labile) groups allows sequential deprotection for stepwise synthesis. Compatibility : Used in automated oligosaccharide synthesis due to Fmoc's compatibility with solid-phase techniques. Applications Neoglycoconjugate synthesis : Fmoc removal exposes C6-OH for subsequent conjugation to proteins/peptides. Glycosidase inhibitor development : Protected glucose derivatives serve as transition-state analogs in enzyme inhibition studies. Dendrimer construction : Enables controlled branching through selective deprotection at C6. The compound's synthesis typically involves: Thioglycoside formation via BF₃·OEt₂-catalyzed coupling of per-O-acetyl-glucose with 4-methylthiophenol. Sequential protection using benzylidene acetal (C4/C6), followed by regioselective benzoylation (C2/C3). Fmoc introduction at C6 through carbodiimide-mediated coupling after benzylidene ring-opening. This derivative exemplifies modern carbohydrate engineering strategies that combine traditional protecting groups with photolabile/base-sensitive groups for precision synthesis. Citations: https://pubmed.ncbi.nlm.nih.gov/8135348/ https://pubchem.ncbi.nlm.nih.gov/compound/1326804-93-6 https://www.rsc.org/suppdata/c8/sc/c8sc01743c/c8sc01743c1.pdf https://pubchem.ncbi.nlm.nih.gov/compound/10411640 https://glycomindsynth.com/product_detail/517/Monosaccharide https://www.bocsci.com/product/4-methylphenyl-2-o-benzoyl-3-4-di-o-benzyl-6-o-9-fluorenylmethoxycarbonyl-339431.html https://synthose.com/products/ML822 https://glycodepot.com/product/4-methylphenyl-2-o-benzoyl-36-di-o-benzyl-4-o-9-fluorenylmethoxycarbonyl-1-thio-%CE%B2-d-glucopyranoside/