[(3aS,5R,6R,7S,7aS)-6,7-bis(acetyloxy)-2-methoxy-2-methyl-hexahydro-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate

• ChemBase ID: 178863
• Molecular Formular: C15H22O10
• Molecular Mass: 362.32918
• Monoisotopic Mass: 362.1212969
• SMILES: [C@@H]12O[C@H]([C@H]([C@@H]([C@@H]1OC(O2)(C)OC)OC(=O)C)OC(=O)C)COC(=O)C
• Canonical SMILES: COC1(C)O[C@H]2[C@@H](O1)[C@@H](OC(=O)C)[C@@H]([C@@H](O2)COC(=O)C)OC(=O)C
• InChI: InChI=1S/C15H22O10/c1-7(16)20-6-10-11(21-8(2)17)12(22-9(3)18)13-14(23-10)25-15(4,19-5)24-13/h10-14H,6H2,1-5H3/t10-,11-,12+,13+,14+,15?/m1/s1
• InChIKey: AUVGRVGPAIFPSA-PEONVUOVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3aS,5R,6R,7S,7aS)-6,7-bis(acetyloxy)-2-methoxy-2-methyl-hexahydro-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate
• IUPAC Traditional name: [(3aS,5R,6R,7S,7aS)-6,7-bis(acetyloxy)-2-methoxy-2-methyl-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate
• Synonyms: 1,2-O-(1-Methoxyethylidene)-β-D-mannopyranose Triacetate; 3,4,6-Tri-O-acetyl-β-D-mannopyranose 1,2-(Methyl Orthoacetate)

Database IDs

• CAS Number: 4435-05-6
• PubChem SID: 164234773
• PubChem CID: 11100531

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 0.422084
• LogD (pH = 7.4): 0.422084
• Log P: 0.422084
• Molar Refractivity: 77.0437 cm^3
• Polarizability: 32.33755 Å^3
• Polar Surface Area: 115.82 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 107-109°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T767000

A stable, crystalline precursor for the preparation of acetobromomannose.

REFERENCES

• Schroter, S., et al.: J. Biol. Chem., 274, 29862 (1999)
• Xue, J., et al.: Bioorg. Med. Chem. Lett., 12, 2015 (1999)
• Schofield, L., et al.: Nature, 418, 785 (1999)