Description

α-D-Mannose Pentaacetate (CAS: 4163-65-9) is a high-purity acetylated derivative of D-mannose, extensively used in carbohydrate chemistry and biochemical research. This crystalline compound, with the molecular formula C₁₆H₂₂O₁₁, is synthesized through the complete acetylation of the hydroxyl groups on α-D-mannopyranose, ensuring exceptional stability and solubility in organic solvents. Ideal for glycosylation reactions, it serves as a key intermediate in the synthesis of complex oligosaccharides, glycoconjugates, and glycomimetics. With a purity grade suitable for pharmaceutical and diagnostic applications, it is rigorously tested via HPLC, NMR, and mass spectrometry to meet industry standards. Packaged under inert conditions to prevent moisture absorption, this product is a must-have for researchers focusing on glycobiology, vaccine development, and drug discovery.

Properties

• CAS Number: 4163-65-9
• Complexity: 599
• IUPAC Name: [(2R,3R,4S,5S,6R)-3,4,5,6-tetraacetoxytetrahydropyran-2-yl]methyl acetate
• InChI: InChI=1S/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13-,14+,15+,16+/m1/s1
• InChI Key: LPTITAGPBXDDGR-OWYFMNJBSA-N
• Exact Mass: 390.11621151
• Molecular Formula: C16H22O11
• Molecular Weight: 390.34
• SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Topological: 141
• Monoisotopic Mass: 390.11621151
• Synonyms: alpha-d-Mannose pentaacetate, DTXSID301313184, DTXCID801743007, 4163-65-9, a-D-Mannose pentaacetate, 1,2,3,4,6-Penta-O-acetyl-alpha-D-mannopyranose, 1,2,3,4,6-Penta-O-acetyl-a-D-mannopyranose, (2R,3S,4S,5R,6R)-6-(acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate, MFCD00069798, 1,2,3,4,6-Penta-O-acetyl-|A-D-mannopyranose, [(2R,3R,4S,5S,6R)-3,4,5,6-tetraacetyloxyoxan-2-yl]methyl acetate, alpha-D-Mannopyranose pentaacetate, a-D-Mannosepentaacetate, 1,2,3,4,6-Penta-O-acetyl-?-D-mannopyranose, |A-D-Mannose pentaacetate, I+/–D-Mannose pentaacetate, alpha -D-Mannose pentaacetate, SCHEMBL116420, LPTITAGPBXDDGR-OWYFMNJBSA-N, AKOS015919016, FS-5921, HY-W039898, MP00476, MP00483, CS-0098156, [(2R,3R,4S,5S,6R)-3,4,5,6-tetraacetoxytetrahydropyran-2-yl]methyl acetate

α-D-Mannose Pentaacetate is widely employed as a protected mannose donor in glycosylation reactions for oligosaccharide synthesis. It is utilized in glycoconjugate vaccine development due to its role in mimicking bacterial and viral carbohydrate epitopes. Researchers also use it as a precursor for mannose-containing probes in glycan array studies and cell-surface labeling. Its stability makes it suitable for mechanistic studies in enzymatic glycosyl transfer reactions.

Safety and Hazards

GHS Hazard Statements

• H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statements

• P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501

Hazard Classes and Categories

• Skin Sens. 1 (100%)
• Eye Irrit. 2 (100%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.