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

• ChemBase ID: 176285
• Molecular Formular: C16H22O11
• Molecular Mass: 390.33928
• Monoisotopic Mass: 390.11621152
• SMILES: O1C([C@H]([C@H]([C@@H]([C@@H]1COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@@H]1OC(OC(=O)C)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• 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
• InChIKey: LPTITAGPBXDDGR-WHWZVRATSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5S)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5S)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate
• Synonyms: 1,2,3,4,6-Pentaacetate D-Mannopyranose; D-Mannopyranose Pentaacetate; 1,2,3,4,6-Penta-O-acetyl-D-mannopyranose

Database IDs

• CAS Number: 25941-03-1
• PubChem SID: 164232195
• PubChem CID: 11811209

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.72691214
• LogD (pH = 7.4): -0.72691214
• Log P: -0.72691214
• Molar Refractivity: 81.6809 cm^3
• Polarizability: 34.419 Å^3
• Polar Surface Area: 140.73 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ether; Ethyl Acetate; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 68-70°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P230100

Used for preparation of glycopyranoside phosphates for treatment of T lymphocyte mediated inflammatory diseases.

REFERENCES

• Detheux, M., et al.: Eur. J. Biochem., 200(2)
• 553 (2)