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

• ChemBase ID: 103335
• Molecular Formular: C8H14O5
• Molecular Mass: 190.19376
• Monoisotopic Mass: 190.08412355
• SMILES: O1C(O[C@H]2O[C@H](CO)[C@H](O)[C@@H]12)(C)C
• Canonical SMILES: OC[C@H]1O[C@H]2[C@@H]([C@H]1O)OC(O2)(C)C
• InChI: InChI=1S/C8H14O5/c1-8(2)12-6-5(10)4(3-9)11-7(6)13-8/h4-7,9-10H,3H2,1-2H3/t4-,5+,6-,7-/m1/s1
• InChIKey: JAUQZVBVVJJRKM-XZBKPIIZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,5R,6S,6aR)-5-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol
• IUPAC Traditional name: (3aR,5R,6S,6aR)-5-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• Synonyms: 1,2-O-Isopropylidene-α-D-xylofuranose; 1,2-O-ISOPROPYLIDENE-α-D-XYLOFURANOSE; 1,2-O-异亚丙基-α-D-呋喃木糖

Database IDs

• CAS Number: 20031-21-4
• MDL Number: MFCD00063295
• Beilstein Number: 81520
• PubChem SID: 162103122; 24857854
• PubChem CID: 88338

CALCULATED PROPERTIES

• Acid pKa: 12.960336
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.59977967
• LogD (pH = 7.4): -0.59978086
• Log P: -0.59977967
• Molar Refractivity: 42.1679 cm^3
• Polarizability: 17.489017 Å^3
• Polar Surface Area: 68.15 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 67-70 °C; 69-71 °C(lit.)
• Boiling Point: 112-114 °C/0.06 mmHg(lit.)
• Optical Rotation: [α]20/D -19±1°, c = 1% in H2O; [α]25/D -19.2°, c = 1 in H2O

Safety Information

• German water hazard class: 3
• 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); 99%
• Grade: purum
• Empirical Formula (Hill Notation): C8H14O5

DETAILS

Sigma Aldrich - 296368

Packaging
10, 25, 100 g in glass bottle

Sigma Aldrich - 59545

Other Notes
Versatile derivative of D-xylose; used as chiral building block, e.g. synthesis of carbohydrate derivatives, derivatives of nucleosides1,2; chain elongation of derivatives by Wittig reaction3,4