(3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-ol

• ChemBase ID: 302439
• Molecular Formular: C8H14O5
• Molecular Mass: 190.19376
• Monoisotopic Mass: 190.08412355
• SMILES: CC1(O[C@@H]2[C@H](OC([C@@H]2O1)O)CO)C
• Canonical SMILES: OC[C@H]1OC([C@H]2[C@@H]1OC(O2)(C)C)O
• InChI: InChI=1S/C8H14O5/c1-8(2)12-5-4(3-9)11-7(10)6(5)13-8/h4-7,9-10H,3H2,1-2H3/t4-,5-,6-,7?/m1/s1
• InChIKey: OYYTWUSIDMJZCP-RKEPMNIXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-ol
• IUPAC Traditional name: (3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• Synonyms: 2,3-O-Isopropylidene-alpha,beta-D-ribofuranose; 2,3-O-异亚丙基-α,β-D-呋喃核糖

Database IDs

• CAS Number: 13199-25-2
• MDL Number: MFCD01075718

CALCULATED PROPERTIES

• Acid pKa: 11.337069
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.5997803
• LogD (pH = 7.4): -0.5998298
• Log P: -0.59977967
• Molar Refractivity: 42.1679 cm^3
• Polarizability: 17.489017 Å^3
• Polar Surface Area: 68.15 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: -27 (c=1 in chloroform)

Safety Information

• TSCA Listed: 否

REFERENCES

• Reaction of this hemiacetal with various organometallic species provides routes to a number of synthetic targets, e.g.: (-)-5-epishikimic acid: Tetrahedron Lett., 35, 5505 (1994); J. Chem. Soc., Perkin 1, 1805 (1997), aminocyclopentitols: Tetrahedron: Asymmetry, 6, 1547 (1995), cyclopentane-type glycosidase inhibitors: J. Org. Chem., 61, 1354 (1996). Reaction with cysteamine leads to diastereomerically pure analogues of the alkaloids castanospermine and australine: Tetrahedron Lett., 37, 49 (1996).