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

• ChemBase ID: 160673
• Molecular Formular: C6H10O5
• Molecular Mass: 162.1406
• Monoisotopic Mass: 162.05282342
• SMILES: [C@H]12[C@@H]([C@H]([C@@H]([C@H](CO1)O2)O)O)O
• Canonical SMILES: O[C@H]1[C@H](O)[C@@H]2CO[C@H]([C@@H]1O)O2
• InChI: InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2/t2-,3-,4+,5-,6-/m1/s1
• InChIKey: TWNIBLMWSKIRAT-VFUOTHLCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
• IUPAC Traditional name: levoglucosan
• Synonyms: 1,6-Anhydro-D-glucose; Levoglucosan; 1,6-Anhydro-D-glucopyranoside; 1,6-Anhydroglucose; Leucoglucosan; NSC 46243; 1,6-Anhydro-β-D-glucopyranose

Database IDs

• CAS Number: 498-07-7
• PubChem SID: 162254808
• PubChem CID: 2724705

CALCULATED PROPERTIES

• Acid pKa: 12.212605
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.7708358
• LogD (pH = 7.4): -1.7708423
• Log P: -1.7708356
• Molar Refractivity: 32.4133 cm^3
• Polarizability: 13.814454 Å^3
• Polar Surface Area: 79.15 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Water
• Apperance: White Solid
• Melting Point: 169-172°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - A648100

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