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

• ChemBase ID: 160998
• Molecular Formular: C9H15N3O5
• Molecular Mass: 245.2325
• Monoisotopic Mass: 245.1011706
• SMILES: [C@H]12[C@@H](C(O[C@@H]1OC(O2)(C)C)(CO)CO)N=[N+]=[N-]
• Canonical SMILES: [N-]=[N+]=N[C@H]1[C@@H]2OC(O[C@H]2OC1(CO)CO)(C)C
• InChI: InChI=1S/C9H15N3O5/c1-8(2)15-5-6(11-12-10)9(3-13,4-14)17-7(5)16-8/h5-7,13-14H,3-4H2,1-2H3/t5-,6-,7-/m0/s1
• InChIKey: GUPBGRHABGKBNJ-ACZMJKKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3aR,6S,6aS)-6-azido-5-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]methanol
• IUPAC Traditional name: [(3aR,6S,6aS)-6-azido-5-(hydroxymethyl)-2,2-dimethyl-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]methanol
• Synonyms: 3-Azido-3-deoxy-4-C-(hydroxymethyl)-1,2-O-(1-methylethylidene)-α-D-erythro-pentofuranose; 3-Azido-3-deoxy-4-hydroxy-methyl-1,2-O-isopropylidene-α-D-ribofuranose

Database IDs

• CAS Number: 247025-10-1
• PubChem SID: 162255133
• PubChem CID: 71313572

CALCULATED PROPERTIES

• Acid pKa: 13.469785
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.6598142
• LogD (pH = 7.4): -0.65981454
• Log P: -0.5457685
• Molar Refractivity: 54.6423 cm^3
• Polarizability: 21.695843 Å^3
• Polar Surface Area: 97.58 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Ethanol; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 110-112°C

Safety Information

• Storage Condition: -20°C Freezer

REFERENCES

• Obika, S., et al.: Bioorg. Med. Chem., 16, 9230 (2008)