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

• ChemBase ID: 92241
• Molecular Formular: C31H30O4
• Molecular Mass: 466.5675
• Monoisotopic Mass: 466.21440944
• SMILES: O1[C@@H](C(c2ccccc2)(c2ccccc2)O)[C@@H](OC1(C)C)C(c1ccccc1)(c1ccccc1)O
• 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-/m1/s1
• InChIKey: OWVIRVJQDVCGQX-VSGBNLITSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 93379-48-7
• MDL Number: MFCD00064467
• Beilstein Number: 3657855
• PubChem SID: 24856048; 24893437; 162078939; 24881569
• PubChem CID: 2725026

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: 192-195 °C; 193-195 °C(lit.)
• Optical Rotation: [α]19/D -62.6°, c = 1 in chloroform; [α]20/D -67±2°, c = 1% in chloroform

Safety Information

• Storage Warning: Irritant
• 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 - D1431

Application
用作不对称催化剂、1光学拆分试剂2以及核磁共振波谱法中的手性位移试剂。3

Sigma Aldrich - 265004

Packaging
1 g in glass bottle
Application
Hydrogen-bonding organocatalyst examined in terms of acidity, deprotonation enthalpies and hydrogen bonding1Catalyst involved in synthesis of cyclopropylamines via addition reactions of Grignard reagents to amides2Reactant or reagent involved in:
• Enantioswitching of catalytic asymmetric hydroboration3
• Synthesis of derivative ligands for asymmetric hydroformylation of alkenes4
• Amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes5
• Addition of deactivated alkyl Grignard reagents to aldehydes6