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  • 265004 - (4R,5R)-2,2-Dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanol

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265004 Aldrich

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

97%

Synonym: (−)-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

  • CAS Number 93379-48-7

  • Empirical Formula (Hill Notation) C31H30O4

  • Molecular Weight 466.57

  •  Beilstein Registry Number 3657855

  •  MDL number MFCD00064467

  •  PubChem Substance ID 24856048

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes, TADDOLs More...
InChI Key   OWVIRVJQDVCGQX-VSGBNLITSA-N
assay   97%
optical activity   [α]19/D −62.6°, c = 1 in chloroform
mp   193-195 °C (lit.)

Description

Packaging

1 g in glass bottle

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 & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

Chiral Diols - Aldrich ChemFiles 2007, 7.9, 13.

Apart from numerous examples using TADDOLs in metal-catalyzed asymmetric reactions, Rawal recently reported that TADDOLs could be used as Brønsted acid organocatalysts in highly stereoselective heter...
Aldrich ChemFiles 2007, 7.9, 13.
Keywords: Addition reactions, Aminations, Asymmetric synthesis, Catalysis, Chemfiles, Substitutions

TADDOL

The chiral auxiliaries TADDOLs (α,α,α,α-tetraaryl-1,3-dioxolane-4,5- dimethanols) developed by Seebach's group have found numerous applications in asymmetric synthesis ranging from utilization as sto...
Keywords: Addition reactions, Applications, Asymmetric synthesis, Catalysis, Chiral auxiliaries, Desymmetrizations, Diels-Alder reaction, Fluorinations, Hydrogenations, Metathesis, Nucleophilic additions, Polymerization reactions, Transesterifications

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