4-[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]-2,2-dimethyl-1,3-dioxolane

• ChemBase ID: 160993
• Molecular Formular: C12H19N3O5
• Molecular Mass: 285.29636
• Monoisotopic Mass: 285.13247072
• SMILES: [C@@H]12[C@@H]([C@H](O[C@@H]1OC(O2)(C)C)C1COC(O1)(C)C)N=[N+]=[N-]
• Canonical SMILES: [N-]=[N+]=N[C@@H]1[C@H](O[C@H]2[C@@H]1OC(O2)(C)C)C1COC(O1)(C)C
• InChI: InChI=1S/C12H19N3O5/c1-11(2)16-5-6(18-11)8-7(14-15-13)9-10(17-8)20-12(3,4)19-9/h6-10H,5H2,1-4H3/t6?,7-,8+,9+,10+/m0/s1
• InChIKey: UZVCUNUCGITLER-DEMCRKGTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]-2,2-dimethyl-1,3-dioxolane
• IUPAC Traditional name: 4-[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2,2-dimethyl-1,3-dioxolane
• Synonyms: 3-Azido-3-deoxy-1,2:5,6-bis-O-(1-methylethylidene)-α-D-glucofuranose; 3-Azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Database IDs

• CAS Number: 13964-23-3
• PubChem SID: 162255128
• PubChem CID: 12775551

CALCULATED PROPERTIES

• Acid pKa: 14.434619
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 1.1786088
• LogD (pH = 7.4): 1.1786088
• Log P: 1.2926544
• Molar Refractivity: 66.6299 cm^3
• Polarizability: 26.564737 Å^3
• Polar Surface Area: 75.58 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow Liquid
• Boiling Point: 106°C

REFERENCES

• Hainrichson, M., et al.: Bioorg. Med. Chem., 13, 5797 (2005)