[(2R,3S,4S,5R,6R)-3,4,6-tris(acetyloxy)-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl acetate

• ChemBase ID: 178198
• Molecular Formular: C20H30O14
• Molecular Mass: 494.4438
• Monoisotopic Mass: 494.16355564
• SMILES: [C@H]1([C@@H]([C@@H]([C@H](O[C@H]1COC(=O)C)OC(=O)C)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C)O)O)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[C@@H]1O[C@@H](C)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C20H30O14/c1-7-13(25)14(26)15(27)19(29-7)34-18-17(31-10(4)23)16(30-9(3)22)12(6-28-8(2)21)33-20(18)32-11(5)24/h7,12-20,25-27H,6H2,1-5H3/t7-,12+,13+,14+,15-,16-,17-,18+,19-,20-/m0/s1
• InChIKey: NZHIGIDTCTXDAY-KIVQRVDVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4S,5R,6R)-3,4,6-tris(acetyloxy)-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4S,5R,6R)-3,4,6-tris(acetyloxy)-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl acetate
• Synonyms: 1,2,3,4-Tetraacetate-6-deoxy-L-galactopyranose; L-Fucose tetraacetate; NSC 119108; 1,2,3,4-Tetra-O-acetyl-L-fucopyranose, 90%

Database IDs

• CAS Number: 24332-95-4
• PubChem SID: 164234108
• PubChem CID: 71752384

CALCULATED PROPERTIES

• Acid pKa: 12.223981
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): -1.8919634
• LogD (pH = 7.4): -1.8919698
• Log P: -1.8919632
• Molar Refractivity: 103.399 cm^3
• Polarizability: 43.665806 Å^3
• Polar Surface Area: 193.58 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Colourless Thick Syrup

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T279255

Used in glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo.

REFERENCES

• Mahal, L., et al.: Science, 276, 1125 (1997)
• Apweiler, R., et al.: Biochim. Biophys. Acta, 1473, 4 (1997)
• Becker, D., et al.: Glycobiology, 13, 41R (1997)