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

• ChemBase ID: 178192
• Molecular Formular: C14H19FO9
• Molecular Mass: 350.2936632
• Monoisotopic Mass: 350.10131041
• SMILES: [C@H]1([C@@H]([C@@H](C(O[C@H]1COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)F
• Canonical SMILES: CC(=O)OC[C@@H]1OC(OC(=O)C)[C@H]([C@H]([C@H]1F)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C14H19FO9/c1-6(16)20-5-10-11(15)12(21-7(2)17)13(22-8(3)18)14(24-10)23-9(4)19/h10-14H,5H2,1-4H3/t10-,11+,12+,13-,14?/m1/s1
• InChIKey: DPGJKBANJUBLLX-RRYROLNDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R)-4,5,6-tris(acetyloxy)-3-fluorooxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4R,5R)-4,5,6-tris(acetyloxy)-3-fluorooxan-2-yl]methyl acetate
• Synonyms: GlcNAc1-b-4GlcNAc1-b-4GlcNAc1-b-4GlcNAc; N,N',N'',N'''-Tetraacetylchitotetraose

Database IDs

• CAS Number: 2706-65-2
• PubChem SID: 164234102
• PubChem CID: 11602731

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.2769458
• LogD (pH = 7.4): -0.2769458
• Log P: -0.2769458
• Molar Refractivity: 70.8373 cm^3
• Polarizability: 29.726597 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: >200°C dec.

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Store in freezer

DETAILS

Toronto Research Chemicals - T276500

Prepared by acetolysis of chitin. Studies have shown this compound to have anti tumor effects.

REFERENCES

• Barker, S.A., et al.: J. Chem. Soc., 2218 (1958)
• Suzuki, K., et al.: Carbohydrate Research, 151, 403 (1986)