[(2R,3R,4R,5S,6S)-3,4,6-tris(acetyloxy)-5-hydroxyoxan-2-yl]methyl acetate

• ChemBase ID: 151403
• Molecular Formular: C14H20O10
• Molecular Mass: 348.3026
• Monoisotopic Mass: 348.10564684
• SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@@H]([C@@H](O1)OC(=O)C)O)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@H]1O[C@@H](OC(=O)C)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)O
• InChI: InChI=1S/C14H20O10/c1-6(15)20-5-10-12(21-7(2)16)13(22-8(3)17)11(19)14(24-10)23-9(4)18/h10-14,19H,5H2,1-4H3/t10-,11+,12-,13-,14-/m1/s1
• InChIKey: SHBHJRVMGYVXKK-XVIXHAIJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5S,6S)-3,4,6-tris(acetyloxy)-5-hydroxyoxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5S,6S)-3,4,6-tris(acetyloxy)-5-hydroxyoxan-2-yl]methyl acetate
• Synonyms: β-D-Mannopyranose 1,3,4,6-tetra-O-acetate; 1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose; 1,3,4,6-Tetraacetate β-D-Mannopyranose; 1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose; β-D-吡喃甘露糖 1,3,4,6-四-O-乙酸酯; 1,3,4,6-四-O-乙酰基-β-D-吡喃甘露糖

Database IDs

• CAS Number: 18968-05-3
• MDL Number: MFCD00012354
• Beilstein Number: 96634
• PubChem SID: 24858784; 162245557
• PubChem CID: 7269409

CALCULATED PROPERTIES

• Acid pKa: 12.317718
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.1680377
• LogD (pH = 7.4): -1.1680428
• Log P: -1.1680375
• Molar Refractivity: 72.5294 cm^3
• Polarizability: 30.56413 Å^3
• Polar Surface Area: 134.66 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 160-161 °C(lit.)
• Optical Rotation: [α]19/D -68°, c = 0.7 in pyridine

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C14H20O10

DETAILS

Sigma Aldrich - 310247

Packaging
100 mg in glass bottle

Toronto Research Chemicals - T282760

An intermediate in the preparation of precursors of 2-[18F]fluoro-2-deoxy-D-glucose for diagnostic use in positron emission tomography.

REFERENCES

• Maschauer, S. et al.: J. Lab. Comp. Radiopharmac., 48, 701 (2005)