(2R,3R,4S)-2-[(1R)-1,2-dihydroxyethyl]oxolane-3,4-diol

• ChemBase ID: 160692
• Molecular Formular: C6H12O5
• Molecular Mass: 164.15648
• Monoisotopic Mass: 164.06847348
• SMILES: C1[C@@H]([C@H]([C@H](O1)[C@@H](CO)O)O)O
• Canonical SMILES: OC[C@H]([C@H]1OC[C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C6H12O5/c7-1-3(8)6-5(10)4(9)2-11-6/h3-10H,1-2H2/t3-,4+,5-,6-/m1/s1
• InChIKey: JNYAEWCLZODPBN-JGWLITMVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S)-2-[(1R)-1,2-dihydroxyethyl]oxolane-3,4-diol
• IUPAC Traditional name: 1,4-dianhydrosorbitol
• Synonyms: 1,4-Anhydro-D-glucitol; 1,4-Anhydroglucitol; 1,4-Sorbitan; 1,4-Anhydro-D-sorbitol

Database IDs

• CAS Number: 27299-12-3
• PubChem SID: 162254827
• PubChem CID: 10953859

CALCULATED PROPERTIES

• Acid pKa: 12.749265
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.5683153
• LogD (pH = 7.4): -2.5683172
• Log P: -2.5683153
• Molar Refractivity: 34.8935 cm^3
• Polarizability: 14.43744 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol
• Apperance: White Solid
• Melting Point: 112-113°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A655525

A useful intermediate in Prostaglandin synthesis.

REFERENCES

• Jeong, G., et al.: App. Biochem. Biotechnol., 137, 935 (2007)