(3aS,5S,6aR)-3a,5-bis(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol

• ChemBase ID: 171923
• Molecular Formular: C9H16O6
• Molecular Mass: 220.21974
• Monoisotopic Mass: 220.09468823
• SMILES: C1(O)[C@H](CO)O[C@@]2(CO)OC(O[C@@H]12)(C)C
• Canonical SMILES: OC[C@@H]1O[C@@]2([C@H](C1O)OC(O2)(C)C)CO
• InChI: InChI=1S/C9H16O6/c1-8(2)14-7-6(12)5(3-10)13-9(7,4-11)15-8/h5-7,10-12H,3-4H2,1-2H3/t5-,6?,7+,9-/m0/s1
• InChIKey: AVVCILZWWPKOLD-FTTNTJTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,5S,6aR)-3a,5-bis(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol
• IUPAC Traditional name: (3aS,5S,6aR)-3a,5-bis(hydroxymethyl)-2,2-dimethyl-dihydro-5H-furo[2,3-d][1,3]dioxol-6-ol
• Synonyms: (3R,4S,5R)-7-(Acetyloxy)-3a,6,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-5-carboxylic Acid Methyl Ester; (3R,4S,5R)-5-Hydroxy-3,4-(isopropylidenedioxy)-1-cyclohexene-1-carboxylic Acid Methyl Ester Acetate; 3,4-(Isopropylidenedioxy) Shikimic Acid Methyl Ester Acetate

Database IDs

• CAS Number: 143308-74-1
• PubChem SID: 164227833
• PubChem CID: 45039611

CALCULATED PROPERTIES

• Acid pKa: 12.838055
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.0555748
• LogD (pH = 7.4): -1.0555763
• Log P: -1.0555747
• Molar Refractivity: 48.5678 cm^3
• Polarizability: 20.00014 Å^3
• Polar Surface Area: 88.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 73-75°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - I870400

3,4-(Isopropylidenedioxy) Shikimic acid methyl ester acetate is a derivative of Shikimic acid (S357100).

REFERENCES

• Smissman, E.E, et al.: Tetrahedron Lett., 44, 4601 (1968)