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

• ChemBase ID: 149458
• Molecular Formular: C12H20O6
• Molecular Mass: 260.2836
• Monoisotopic Mass: 260.12598836
• SMILES: CC1(OCC(O1)[C@@H]1[C@H]2C(C(O1)O)OC(O2)(C)C)C
• Canonical SMILES: OC1O[C@@H]([C@H]2C1OC(O2)(C)C)C1COC(O1)(C)C
• InChI: InChI=1S/C12H20O6/c1-11(2)14-5-6(16-11)7-8-9(10(13)15-7)18-12(3,4)17-8/h6-10,13H,5H2,1-4H3/t6?,7-,8+,9?,10?/m1/s1
• InChIKey: JWWCLCNPTZHVLF-RGJLLFKYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,6aS)-6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-ol
• IUPAC Traditional name: (6R,6aS)-6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• Synonyms: D-Mannose diacetonide; 2,3:5,6-Di-O-isopropylidene-α-D-mannofuranose; 2,3:5,6-二异亚丙基-D-甘露糖; 双丙酮-D-甘露糖

Database IDs

• CAS Number: 14131-84-1
• MDL Number: MFCD00134206
• Beilstein Number: 84382
• PubChem SID: 162243623; 24862256
• PubChem CID: 16212320

CALCULATED PROPERTIES

• Acid pKa: 11.336936
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.47230938
• LogD (pH = 7.4): 0.47225985
• 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: 121-126 °C; 125-126 °C (dec.)(lit.)
• Optical Rotation: [α]20/D +23°, c = 1 in acetone; [α]20/D +24±2°, c = 1% in acetone

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: ≥99.0% (GC); 97%
• Grade: puriss.
• Empirical Formula (Hill Notation): C12H20O6

DETAILS

Sigma Aldrich - 361763

Application
Protected mannose intermediate used in the syntheses of ovalicin1 and of the sugar core of hikizimycin.2
Packaging
5 g in glass bottle

Sigma Aldrich - 38413

Features and Benefits
Use as chiral building block1,2; Preparation of the mannosyl fluoride and α-mannosides3; Wittig reaction4