[(4R,5R)-5-[hydroxybis(naphthalen-2-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]bis(naphthalen-2-yl)methanol

• ChemBase ID: 138675
• Molecular Formular: C47H38O4
• Molecular Mass: 666.80222
• Monoisotopic Mass: 666.2770097
• SMILES: CC1(O[C@H]([C@@H](O1)C(c1ccc2ccccc2c1)(c1ccc2ccccc2c1)O)C(c1ccc2ccccc2c1)(c1ccc2ccccc2c1)O)C
• Canonical SMILES: CC1(C)O[C@H]([C@@H](O1)C(c1ccc2c(c1)cccc2)(c1ccc2c(c1)cccc2)O)C(c1ccc2c(c1)cccc2)(c1ccc2c(c1)cccc2)O
• InChI: InChI=1S/C47H38O4/c1-45(2)50-43(46(48,39-23-19-31-11-3-7-15-35(31)27-39)40-24-20-32-12-4-8-16-36(32)28-40)44(51-45)47(49,41-25-21-33-13-5-9-17-37(33)29-41)42-26-22-34-14-6-10-18-38(34)30-42/h3-30,43-44,48-49H,1-2H3/t43-,44-/m1/s1
• InChIKey: QWADMRIAKWGVBF-NDOUMJCMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4R,5R)-5-[hydroxybis(naphthalen-2-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]bis(naphthalen-2-yl)methanol
• IUPAC Traditional name: [(4R,5R)-5-[hydroxybis(naphthalen-2-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]bis(naphthalen-2-yl)methanol
• Synonyms: (-)-DINOL; (-)-2,3-O-Isopropylidene-1,1,4,4-tetra(2-naphthyl)-L-threitol; (4R,5R)-2,2-Dimethyl-α,α,α′,α′-tetra(2-naphthyl)dioxolane-4,5-dimethanol; (-)-2,3-O-异亚丙基-1,1,4,4-四(2-萘基)-L-苏糖醇; (4R,5R)-2,2-二甲基-α,α,α′,α′-四(2-萘基)二氧戊环-4,5-二甲醇

Database IDs

• CAS Number: 137365-09-4
• MDL Number: MFCD00142337
• Beilstein Number: 6168481
• PubChem SID: 162232926; 24881543; 24864538
• PubChem CID: 10919449

CALCULATED PROPERTIES

• Acid pKa: 12.040149
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 9.778507
• LogD (pH = 7.4): 9.778498
• Log P: 9.778507
• Molar Refractivity: 202.4584 cm^3
• Polarizability: 84.29158 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 213-216 °C(lit.)
• Optical Rotation: [α]20/D -116±2°, c = 1% in ethyl acetate; [α]20/D -116°, c = 1 in ethyl acetate

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% (sum of enantiomers, HPLC); 99%
• Optical Purity: ee: 99% (HPLC); enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Empirical Formula (Hill Notation): C47H38O4

DETAILS

Sigma Aldrich - 59490

Packaging
1 g in glass bottle

Sigma Aldrich - 393754

Application
Reagent for the highly enantioselective addition of primary alkyl Grignards to ketones.1