(3R,3aR,6R,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol

• ChemBase ID: 149240
• Molecular Formular: C6H10O4
• Molecular Mass: 146.1412
• Monoisotopic Mass: 146.0579088
• SMILES: C1[C@H]([C@@H]2[C@H](O1)[C@@H](CO2)O)O
• Canonical SMILES: O[C@@H]1CO[C@H]2[C@@H]1OC[C@H]2O
• InChI: InChI=1S/C6H10O4/c7-3-1-9-6-4(8)2-10-5(3)6/h3-8H,1-2H2/t3-,4-,5-,6-/m1/s1
• InChIKey: KLDXJTOLSGUMSJ-KVTDHHQDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,3aR,6R,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol
• IUPAC Traditional name: (3R,3aR,6R,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol
• Synonyms: Isomannide; 1,4:3,6-Dianhydro-D-mannitol; 异甘露糖醇; 1,4:3,6-双脱水甘露醇

Database IDs

• CAS Number: 641-74-7
• EC Number: 211-374-1
• MDL Number: MFCD10698761
• Beilstein Number: 80509
• PubChem SID: 24860075; 24859780; 162243408
• PubChem CID: 10975624

CALCULATED PROPERTIES

• Acid pKa: 13.034376
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.4066117
• LogD (pH = 7.4): -1.4066128
• Log P: -1.4066117
• Molar Refractivity: 31.3834 cm^3
• Polarizability: 13.101962 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 80-85 °C(lit.); 82-87 °C
• Optical Rotation: [α]20/D +89±2°, c = 5% in H2O; [α]25/D +89°, c = 3 in H2O

Safety Information

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

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); 95%
• Grade: purum
• Empirical Formula (Hill Notation): C6H10O4

DETAILS

Sigma Aldrich - 329266

Packaging
25, 100 g in poly bottle

Sigma Aldrich - 33427

Other Notes
Preparation of monomers used in polymer chemistry1; Building block2