(3aR,6aR)-6-(hydroxymethyl)-2,2,3a-trimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-one

• ChemBase ID: 173842
• Molecular Formular: C9H14O5
• Molecular Mass: 202.20446
• Monoisotopic Mass: 202.08412355
• SMILES: [C@@]12([C@H](OC(O1)(C)C)C(OC2=O)CO)C
• Canonical SMILES: OCC1OC(=O)[C@]2([C@@H]1OC(O2)(C)C)C
• InChI: InChI=1S/C9H14O5/c1-8(2)13-6-5(4-10)12-7(11)9(6,3)14-8/h5-6,10H,4H2,1-3H3/t5?,6-,9-/m1/s1
• InChIKey: JTORQZQZELCRKV-NTNLOPJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,6aR)-6-(hydroxymethyl)-2,2,3a-trimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-one
• IUPAC Traditional name: (3aR,6aR)-6-(hydroxymethyl)-2,2,3a-trimethyl-dihydrofuro[3,4-d][1,3]dioxol-4-one
• Synonyms: 2-C-Methyl-2,3-O-(1-methylethylidene)-D-ribonic Acid γ-Lactone; 2,3-O-Isopropylidene-2-C-methyl-D-ribonic Acid γ-Lactone; 2-C-Methyl-2,3-O-isopropylidene-D-ribono-1,4-lactone

Database IDs

• CAS Number: 23709-41-3
• PubChem SID: 164229752
• PubChem CID: 71750398

CALCULATED PROPERTIES

• Acid pKa: 14.562921
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.020252258
• LogD (pH = 7.4): 0.020252228
• Log P: 0.020252258
• Molar Refractivity: 45.7366 cm^3
• Polarizability: 18.770006 Å^3
• Polar Surface Area: 64.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M314680

2-C-Methyl-2,3-O-isopropylidene-D-ribono-1,4-lactone is used in the synthesis of carbon-branched carbohydrate chirons: enantiomers of 2-C-Methyl-ribono-1,4-lactone (M325961) and 2-C-Methyl-arabinonolactone, as Neplanocyn A intermediates, a potential anti-

REFERENCES

• Carson, J., et al.: J. Med. Chem., 35, 2855 (1992)
• O'Hagan, D., et al.: Nat. Prod. Rev., 17, 435 (1992)