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

• ChemBase ID: 148702
• Molecular Formular: C8H12O5
• Molecular Mass: 188.17788
• Monoisotopic Mass: 188.06847348
• SMILES: CC1(O[C@@H]2[C@H](OC(=O)[C@@H]2O1)CO)C
• Canonical SMILES: OC[C@H]1OC(=O)[C@H]2[C@@H]1OC(O2)(C)C
• InChI: InChI=1S/C8H12O5/c1-8(2)12-5-4(3-9)11-7(10)6(5)13-8/h4-6,9H,3H2,1-2H3/t4-,5-,6-/m1/s1
• InChIKey: NHHKFJCWLPPNCN-HSUXUTPPSA-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-one
• IUPAC Traditional name: (3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• Synonyms: 2,3-O-Isopropylidene-D-ribono-1,4-lactone; 2,3-O-Isopropylidene-D-ribonic γ-lactone; 2,3-O-Isopropylidene-D-ribonic γ-lactone; 2,3-O-Isopropylidene-D-ribono-1,4-lactone; 2,3-O-异亚丙基-D-核糖酸-1,4-内酯; 2,3-O-异亚丙基-D-核糖酸 γ-内酯; 2,3-O-异亚丙基-D-核糖酸·γ-内酯; 2,3-O-异亚丙基-D-核糖酸-1,4-内酯

Database IDs

• CAS Number: 30725-00-9
• MDL Number: MFCD00080793
• Beilstein Number: 10090
• PubChem SID: 162242877; 24863253
• PubChem CID: 1268067

CALCULATED PROPERTIES

• Acid pKa: 14.5634775
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.41251364
• LogD (pH = 7.4): -0.41251364
• Log P: -0.4125136
• Molar Refractivity: 41.0233 cm^3
• Polarizability: 16.957924 Å^3
• Polar Surface Area: 64.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 135-138 °C(lit.); 135-139 °C
• Optical Rotation: [α]20/D -68±1°, c = 2% in pyridine; [α]20/D -69°, c = 2 in pyridine

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (TLC); 99%
• Grade: purum
• Empirical Formula (Hill Notation): C8H12O5

DETAILS

Sigma Aldrich - 373699

Packaging
1 g in glass bottle
250 mg in glass bottle
Application
Important raw material for the synthesis of C-nucleosides,1 prostanoids,2 and GABA analogs via homochiral 2-piperidones.3 Starting material for the preparation of biochemical compounds including C-nucleosides, such as neplanocin A, and GABA analogs, via homochiral 2-piperidones.4,5,6

Sigma Aldrich - 59485

Other Notes
Chiral building block for the synthesis of nucleosides and other compounds1,2,3