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

• ChemBase ID: 171511
• Molecular Formular: C16H22O11
• Molecular Mass: 390.33928
• Monoisotopic Mass: 390.11621152
• SMILES: [C@@H]1([C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)COC(=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)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+/m0/s1
• InChIKey: LPTITAGPBXDDGR-ZVDSWSACSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S,3R,4S,5R,6S)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2S,3R,4S,5R,6S)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate
• Synonyms: Idopyranose Pentaacetate; Pentaacetate α-L-Idopyranose; α-L-Idopyranose Pentaacetate

Database IDs

• CAS Number: 2152-77-4
• PubChem SID: 164227421
• PubChem CID: 12236020

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: Acetone; Dichloromethane; DMF; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 94-96°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I192500

α-L-Idopyranose pentaacetate is used in the synthesis of mucopolysaccharides as antagonists agents.

REFERENCES

• Hopwood., et al.: Clinica Chem. Acta, 123, 241 (1982)
• Ogamo., et al.: Carbohydr. Res., 105 (1982)