[(4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]diphenylmethanol

• ChemBase ID: 145628
• Molecular Formular: C31H30O4
• Molecular Mass: 466.5675
• Monoisotopic Mass: 466.21440944
• SMILES: CC1(O[C@@H]([C@H](O1)C(c1ccccc1)(c1ccccc1)O)C(c1ccccc1)(c1ccccc1)O)C
• Canonical SMILES: OC(c1ccccc1)(c1ccccc1)[C@H]1OC(O[C@@H]1C(c1ccccc1)(c1ccccc1)O)(C)C
• InChI: InChI=1S/C31H30O4/c1-29(2)34-27(30(32,23-15-7-3-8-16-23)24-17-9-4-10-18-24)28(35-29)31(33,25-19-11-5-12-20-25)26-21-13-6-14-22-26/h3-22,27-28,32-33H,1-2H3/t27-,28-/m0/s1
• InChIKey: OWVIRVJQDVCGQX-NSOVKSMOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]diphenylmethanol
• IUPAC Traditional name: [(4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]diphenylmethanol
• Synonyms: (+)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-D-threitol; (+)-trans-α,α′-(2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol); (4S,5S)-4,5-Bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane; (4S,5S)-2,2-Dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanol; (+)-2,3-O-异亚丙基-1,1,4,4-四苯基-D-苏糖醇; (+)-反式-α,α′-(2,2-二甲基-1,3-二氧戊环-4,5-二基)双(二苯基甲醇); (4S,5S)-4,5-双(二苯基羟甲基)-2,2-二甲基二氧戊环; (4S,5S)-2,2-二甲基--1,3-二氧戊环-4,5-二基)双(二苯基甲醇)

Database IDs

• CAS Number: 93379-49-8
• MDL Number: MFCD00010079
• Beilstein Number: 4724097
• PubChem SID: 24881572; 24856047; 162239833
• PubChem CID: 9852051

CALCULATED PROPERTIES

• Acid pKa: 12.106078
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 5.8206005
• LogD (pH = 7.4): 5.820592
• Log P: 5.8206005
• Molar Refractivity: 136.6576 cm^3
• Polarizability: 53.904915 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 193-196 °C; 193-196 °C(lit.)
• Optical Rotation: [α]19/D +67°, c = 1 in chloroform; [α]20/D +67±2°, c = 1% in chloroform

Safety Information

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

Product Information

• Purity: ≥97.0% (sum of enantiomers, HPLC); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C31H30O4

DETAILS

Sigma Aldrich - 264997

Packaging
1 g in glass bottle
250 mg in glass bottle
Application
Ligand for enantioselective Lewis-acid mediated Diels-Alder,1 allyltitanation of aldehydes,2 and Michael-Mukaiyama additions promoted by chiral Ti-complexes.3

Sigma Aldrich - 59534

Other Notes
Chiral ligand; used in the preparation of a chiral titanium catalyst employed for asymmetric additions of alkyl groups to aldehydes 1,2