(3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol

• ChemBase ID: 68495
• Molecular Formular: C12H20O6
• Molecular Mass: 260.2836
• Monoisotopic Mass: 260.12598836
• SMILES: O1[C@@H]2[C@H](OC1(C)C)[C@H](O)[C@H](O2)[C@@H]1OC(OC1)(C)C
• Canonical SMILES: O[C@@H]1[C@H](O[C@H]2[C@@H]1OC(O2)(C)C)[C@H]1COC(O1)(C)C
• InChI: InChI=1S/C12H20O6/c1-11(2)14-5-6(16-11)8-7(13)9-10(15-8)18-12(3,4)17-9/h6-10,13H,5H2,1-4H3/t6-,7-,8-,9-,10-/m1/s1
• InChIKey: KEJGAYKWRDILTF-VVULQXIFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol
• IUPAC Traditional name: (3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• Synonyms: 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose; 1,2:5,6-Di-O-isopropylidene-α-D-allofuranose; 1,2:5,6-双-O-异丙叉基-α-D-异呋喃糖

Database IDs

• CAS Number: 2595-05-3
• MDL Number: MFCD00135634
• Beilstein Number: 1345413
• PubChem SID: 24857855; 162034226
• PubChem CID: 7157054

CALCULATED PROPERTIES

• Acid pKa: 12.956559
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.47231
• LogD (pH = 7.4): 0.4723088
• Log P: 0.47231
• Molar Refractivity: 60.3374 cm^3
• Polarizability: 24.877773 Å^3
• Polar Surface Area: 66.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 73-76 °C; 73-76 °C(lit.)
• Optical Rotation: [α]20/D +37±1°, c = 1% in chloroform; [α]25/D +36°, c = 1 in chloroform

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); 95+%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C12H20O6

DETAILS

Sigma Aldrich - 296376

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 38404

Other Notes
Chiral building block; some recent applications1,2,3