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

• ChemBase ID: 302440
• Molecular Formular: C24H32O5Si
• Molecular Mass: 428.59338
• Monoisotopic Mass: 428.20190066
• SMILES: CC1(O[C@@H]2[C@H](OC([C@@H]2O1)O)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)C
• Canonical SMILES: OC1O[C@@H]([C@@H]2[C@H]1OC(O2)(C)C)CO[Si](C(C)(C)C)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C24H32O5Si/c1-23(2,3)30(17-12-8-6-9-13-17,18-14-10-7-11-15-18)26-16-19-20-21(22(25)27-19)29-24(4,5)28-20/h6-15,19-22,25H,16H2,1-5H3/t19-,20-,21-,22?/m1/s1
• InChIKey: OOVHEXLXHQNNLL-NJTYFVPYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,6R,6aR)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-ol
• IUPAC Traditional name: (3aR,6R,6aR)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• Synonyms: 5-O-tert-Butyldiphenylsilyl-2,3-O-isopropylidene-alpha,beta-D-ribofuranose; 5-O-叔丁基联苯基硅烷-2,3-O-异亚丙基-α,β-D-呋喃核糖

Database IDs

• CAS Number: 141607-35-4
• MDL Number: MFCD01075719

CALCULATED PROPERTIES

• Acid pKa: 11.33733
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 5.4085994
• LogD (pH = 7.4): 5.40855
• Log P: 5.4086
• Molar Refractivity: 111.4044 cm^3
• Polarizability: 46.88169 Å^3
• Polar Surface Area: 57.15 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: -28 (c=1.5 in chloroform)

Safety Information

• TSCA Listed: 否

REFERENCES

• Reaction with heteroaryllithium species provides a convenient method for synthesis of C-azanuleosides: J. Org. Chem., 61, 6079 (1996).