(1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-6,8-dioxabicyclo[3.2.1]octane

• ChemBase ID: 160699
• Molecular Formular: C27H28O5
• Molecular Mass: 432.50822
• Monoisotopic Mass: 432.193674
• SMILES: [C@H]12[C@@H]([C@H]([C@@H]([C@H](CO1)O2)OCc1ccccc1)OCc1ccccc1)OCc1ccccc1
• Canonical SMILES: c1ccc(cc1)CO[C@@H]1[C@@H](OCc2ccccc2)[C@H]2OC[C@@H]([C@H]1OCc1ccccc1)O2
• InChI: InChI=1S/C27H28O5/c1-4-10-20(11-5-1)16-28-24-23-19-31-27(32-23)26(30-18-22-14-8-3-9-15-22)25(24)29-17-21-12-6-2-7-13-21/h1-15,23-27H,16-19H2/t23-,24-,25+,26-,27-/m1/s1
• InChIKey: JSRSLTCFTYHIRT-IURCNINISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-6,8-dioxabicyclo[3.2.1]octane
• IUPAC Traditional name: (1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-6,8-dioxabicyclo[3.2.1]octane
• Synonyms: 1,6-Anhydro-2,3,4-tris-O-(phenylmethyl)-β-D-glucopyranose; Tri-O-benzyllevoglucosan; 1,6-Anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose

Database IDs

• CAS Number: 10548-46-6
• PubChem SID: 162254834
• PubChem CID: 10884532

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 5.331963
• LogD (pH = 7.4): 5.331963
• Log P: 5.331963
• Molar Refractivity: 120.5047 cm^3
• Polarizability: 48.082703 Å^3
• Polar Surface Area: 46.15 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White Solid
• Melting Point: 81-84°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A658750

1,6-Anhydrohexopyranoses have proven to be valuable synthons for the preparation of biologically important and structurally diverse products (e.g. rifamycin S, indanomycin, thromboxane B2, (+)-biotin, tetrodotoxin, quinone, and macrolide antibiotics) as

REFERENCES

• Fraser-Reid, B., et al. J. Am. Chem. Soc. 106, 731 (1984)
• Edwards, M.P., et al. J. Org. Chem. 49, 3503 (1984)
• Kelly, A.G., and Roberts, J.S. J. Chem. Soc., Chem. Commun. 228, (1984)
• Ogawa, T., et al. Carbohydr. Res. 57, C31 (1984)
• Isobe, M., et al. Te