(3aS,4R,6R)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-ol

• ChemBase ID: 163264
• Molecular Formular: C14H28O5Si
• Molecular Mass: 304.45462
• Monoisotopic Mass: 304.17060053
• SMILES: [C@H]12C([C@H](O[C@H]1O)CO[Si](C)(C)C(C)(C)C)OC(O2)(C)C
• Canonical SMILES: O[C@@H]1O[C@@H](C2[C@@H]1OC(O2)(C)C)CO[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C14H28O5Si/c1-13(2,3)20(6,7)16-8-9-10-11(12(15)17-9)19-14(4,5)18-10/h9-12,15H,8H2,1-7H3/t9-,10?,11+,12-/m1/s1
• InChIKey: JJLRGSYXWAKGJM-SGUBAKSOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,4R,6R)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-ol
• IUPAC Traditional name: (3aS,4R,6R)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• Synonyms: 5-O-[(1,1-Dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-D-ribose; 5-O-tert-Butyldimethylsilyl-2,3-O-isopropylidene-D-ribose

Database IDs

• CAS Number: 68703-51-5
• PubChem SID: 162257399
• PubChem CID: 71314364

CALCULATED PROPERTIES

• Acid pKa: 11.33733
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.2563994
• LogD (pH = 7.4): 2.2563498
• Log P: 2.2564
• Molar Refractivity: 72.016 cm^3
• Polarizability: 31.439545 Å^3
• Polar Surface Area: 57.15 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Low Melting Solid or Oil at Room Temperature
• Melting Point: 34-35°C
• Boiling Point: 100-102°C/1 mm

Safety Information

• Storage Condition: -20°C Freezer

REFERENCES

• Chu, C., et al.: Bioorg. Med. Chem. Lett., 13, 9 (2003)
• Kim, Y., et al.: J. Med. Chem., 51, 3934 (2003)