Description

Methyl 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranoside (CAS No. 17791-37-6) is a highly specialized carbohydrate derivative extensively used in synthetic organic chemistry and glycoscience research. This compound, with the molecular formula C₃₅H₃₈O₆, features a protected glucose scaffold with benzyl groups at the 2, 3, 4, and 6 positions, rendering it a versatile intermediate for the synthesis of complex oligosaccharides and glycoconjugates. Its alpha-configuration and methoxy group at the anomeric center make it particularly valuable for stereocontrolled glycosylation reactions. The benzyl protecting groups enhance solubility in organic solvents and provide stability under a wide range of reaction conditions. This product is characterized by high purity (>95%) and is supplied as a white to off-white crystalline powder, ideal for precision applications in pharmaceutical development, glycobiology, and chemical biology research.

Properties

• CAS Number: 17791-37-6
• Complexity: 680
• IUPAC Name: (2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-2-(benzyloxymethyl)-6-methoxy-tetrahydropyran
• InChI: InChI=1S/C35H38O6/c1-36-35-34(40-25-30-20-12-5-13-21-30)33(39-24-29-18-10-4-11-19-29)32(38-23-28-16-8-3-9-17-28)31(41-35)26-37-22-27-14-6-2-7-15-27/h2-21,31-35H,22-26H2,1H3/t31-,32-,33+,34-,35+/m1/s1
• InChI Key: IXEBJCKOMVGYKP-KJQSSVQNSA-N
• Exact Mass: 554.26683893
• Molecular Formula: C35H38O6
• Molecular Weight: 554.7
• SMILES: CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Topological: 55.4
• Monoisotopic Mass: 554.26683893
• Synonyms: 17791-37-6, methyl 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranoside, Methyl 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranoside, (2S,3R,4S,5R,6R)-2-methoxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane, (2R,3R,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran, IXEBJCKOMVGYKP-KJQSSVQNSA-N, 1361201-96-8, SCHEMBL7148930, CHEMBL4649702, DTXSID50445588, Methyl 2,3,4,6-Tetrakis-O-(phenylmethyl)-|A-D-glucopyranoside, HY-W337198, MM06624, BS-27516, V10126, Methyl 2,3,4,6-tetra-O-benzyl–D-glucopyranoside, METHYL 2,3,4,6-TETRA-O-BENZYL-?-D-GLUCOPYRANOSIDE

Methyl 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranoside is widely employed as a key building block in the synthesis of glycosides, glycoproteins, and other carbohydrate-based molecules. It serves as a critical intermediate in the preparation of complex oligosaccharides for vaccine development and drug discovery. Researchers utilize this compound in glycosylation reactions to study enzyme mechanisms and carbohydrate-protein interactions. Its stability and reactivity make it suitable for automated solid-phase oligosaccharide synthesis (SPOS). Additionally, it is used in the development of glycosidase inhibitors and other therapeutic agents targeting carbohydrate-mediated biological processes.

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