(3R,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyoxolan-2-one

• ChemBase ID: 171905
• Molecular Formular: C9H14O6
• Molecular Mass: 218.20386
• Monoisotopic Mass: 218.07903817
• SMILES: [C@@H]1(C([C@H](OC1=O)[C@@H]1COC(O1)(C)C)O)O
• Canonical SMILES: O=C1O[C@@H](C([C@@H]1O)O)[C@@H]1COC(O1)(C)C
• InChI: InChI=1S/C9H14O6/c1-9(2)13-3-4(15-9)7-5(10)6(11)8(12)14-7/h4-7,10-11H,3H2,1-2H3/t4-,5?,6+,7+/m0/s1
• InChIKey: JNTPPVKRHGNFKM-LMMQKCLSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyoxolan-2-one
• IUPAC Traditional name: (3R,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyoxolan-2-one
• Synonyms: 5,6-O-Isopropylidene-L-gulono-1,4-lactone

Database IDs

• CAS Number: 94697-68-4
• PubChem SID: 164227815
• PubChem CID: 71749608

CALCULATED PROPERTIES

• Acid pKa: 11.632735
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.042849
• LogD (pH = 7.4): -1.042874
• Log P: -1.0428486
• Molar Refractivity: 46.9858 cm^3
• Polarizability: 19.47009 Å^3
• Polar Surface Area: 85.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 166-170°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I868400

A useful starting material for the synthesis of an array of compounds modified in the 2 and 3 positions.

REFERENCES

• Vekemans, J.A.J., et al.: Recl. Trav. Chim. Pays-Bas, 104, 266 (1985)
• Hubschwerlen, Synthesis, 962 (1986)