265004

(4R,5R)-2,2-Dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanol

97%

• Synonym(s): (−)-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, TADDOL
• Empirical Formula (Hill Notation): C₃₁H₃₀O₄
• CAS Number: 93379-48-7
• Molecular Weight: 466.57
• Beilstein: 3657855
• MDL number: MFCD00064467
• PubChem Substance ID: 24856048

Properties

• Quality Level: 100
• Assay: 97%
• optical activity: [α]19/D −62.6°, c = 1 in chloroform
• mp: 193-195 °C (lit.)
• SMILES string: CC1(C)O[C@H]([C@@H](O1)C(O)(c2ccccc2)c3ccccc3)C(O)(c4ccccc4)c5ccccc5
• 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
• InChI key: OWVIRVJQDVCGQX-VSGBNLITSA-N

Description

Application

Hydrogen-bonding organocatalyst examined in terms of acidity, deprotonation enthalpies and hydrogen bonding

Catalyst involved in synthesis of cyclopropylamines via addition reactions of Grignard reagents to amides

Reactant or reagent involved in:

• Enantioswitching of catalytic asymmetric hydroboration
• Synthesis of derivative ligands for asymmetric hydroformylation of alkenes
• Amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes
• Addition of deactivated alkyl Grignard reagents to aldehydes

Safety Information

• Storage Class Code: 13 - Non Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves