63126-29-4

Basic information

• Product Name: (4R,5R)-4,5-DI(DIMETHYLAMINOCARBONYL)-2,2-DIMETHYLDIOXOLANE, 99+%
• Synonyms: (4R,5R)-4,5-DI(DIMETHYLAMINOCARBONYL)-2,2-DIMETHYLDIOXOLANE, 99+%;(4r-trans)-n,n,n',n',2,2-hexamethyl-1,3-dioxolane-4,5-dicarboxamide;R,R-N,N,N',N',2,2-hexaMethyl-1,3-Dioxolane-4,5-dicarboxaMide;(4R,5R)-N,N,N',N'-2,2-Hexamethyl-1,3-dioxolane-4,5-dica rboxamide
• CAS NO: 63126-29-4
• Molecular Formula: C₁₁H₂₀N₂O₄
• Molecular Weight: 244.2875
• Mol File: 63126-29-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 88 °C
• Boiling Point: 387.21°C (rough estimate)
• Flash Point: 184°C
• Appearance: White/Crystalline Powder
• Density: 1.1583 (rough estimate)
• Refractive Index: 1.4620 (estimate)
• CAS DataBase Reference: (4R,5R)-4,5-DI(DIMETHYLAMINOCARBONYL)-2,2-DIMETHYLDIOXOLANE, 99+%(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5R)-4,5-DI(DIMETHYLAMINOCARBONYL)-2,2-DIMETHYLDIOXOLANE, 99+%(63126-29-4)
• EPA Substance Registry System: (4R,5R)-4,5-DI(DIMETHYLAMINOCARBONYL)-2,2-DIMETHYLDIOXOLANE, 99+%(63126-29-4)

Safety Data

• Hazardous Substances Data: 63126-29-4(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Upstream product

• 122137-20-6 (4R,5R)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarbaldehyde 
• 26549-65-5 N,N,N',N'-tetramethyl L-tartramide 
• 77-76-9 2,2-dimethoxy-propane 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 124-40-3 dimethyl amine 

Downstream Products

• 167640-48-4 (4R,5R)-4-benzoyl-5--2,2-dimethyl-1,3-dioxolane 
• 167282-09-9 (-)-((4R,5R)-5-benzoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methanone 
• 63126-30-7 (4S,5S)-4,5-bis(aminomethyl)-N⁴,N⁴,N⁵,N⁵-2,2-hexamethyl-1,3-dioxolane 
• 861853-90-9 (4R,5R)-2,2-dimethyl-4,5-bis(3,4-dimethylbenzoyl)-1,3-dioxolane 
• 861853-88-5 (-)-((4R,5R)-5-(4-methoxy-benzoyl)-2,2-dimethyl-[1,3]dioxolan-4-yl)-(4-methoxy-phenyl)-methanone 
• 861853-89-6 (-)-((4R,5R)-2,2-dimethyl-5-(4-methyl-benzoyl)-[1,3]dioxolan-4-yl)-p-tolyl-methanone 
• 647027-99-4 (4S,5S)-4,5-bis[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane 
• 861853-86-3 (4S,5S)-4,5-Bis-((R)-methoxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxolane 
• 861853-98-7 (4S,5S)-4,5-Bis-((R)-methoxy-p-tolyl-methyl)-2,2-dimethyl-[1,3]dioxolane 
• 861853-97-6 (4S,5S)-4,5-Bis-[(R)-methoxy-(4-methoxy-phenyl)-methyl]-2,2-dimethyl-[1,3]dioxolane 
• 861853-99-8 (4S,5S)-4,5-Bis-[(R)-(3,4-dimethyl-phenyl)-methoxy-methyl]-2,2-dimethyl-[1,3]dioxolane 

Relevant articles and documents

Tartrate- and imidazole-derived diketones and diols: Preparation and stability constants of their Cu2+ complexes

Overall, six tartrate- and imidazole-derived ketones and diols were synthesized in a stepwise manner as model compounds for the coordination of Cu2+ ions. The stability constants of copper(II) complexes were studied spectrophotometrically. It was found that the two model structures coordinate Cu2+ ions differentially. Graphical abstract: [Figure not available: see fulltext.]

Preparation and Structural Analysis of Several New α,α,α',α'-Tetraaryl-1,3-dioxolane-4,5-dimethanols (TADDOL's) and TADDOL Analogs, Their Evaluation as Titanium Ligands in the Enantioselective Addition of Methyltitanium and Diethylzinc Reagents to Benzaldehyde, and Refinement of ...

Preparation and screening of twenty new ligands, all analogs of α,α,α',α'-tetraaryl-1,3-dioxolane-4,5-dimethanol (TADDOL), for the Ti-catalyzed asymmetric addition of methyltri(isopropoxy)titanium and diethylzinc to benzaldehyde are described.These ligands have the dioxolane ring of the TADDOL's replaced by cyclobutane, cyclopentane, cyclohexene, cyclohexane, bicycloheptene and -heptane and bicyclooctene and -octane moieties; several have H-atoms or alkyl groups in place of the aryl groups, and nine of them have C2 symmetry.X-Ray crystallography and molecular mechanics are used to analyze the structure of the ligands, and two structural features appear to correlate with selectivity: i) the torsion angle for the chelating O-atom and the ortho-C-atom of the axial Ph group (a small, ca. 19 deg, angle is optimum, Fig. 8) and ii) the "degree of perpendicularity" of the axial Ph group (Fig. 9).Competition experiments indicate that TADDOL 1a catalyzes both the methyltitanium and diethylzinc additions >/= 50 times faster than the related dioxolane analogs 12a, 12c, and 12e (Scheme 7), indicating that both axial and equatorial aryl groups (see Footnote 6) are necessary for ligand-accelerated catalysis of these reactions.A refined mechanistic hypotesis is presented (Fig. 10) to explain the selectivities observed for these new ligands.Our analysis suggests that a combination of structural features appear necessary for good catalytic efficiency and high selectivity.These features, especially the rather subtle conformational effects, appear to be optimized (among the ligands tested) in the TADDOL's.

TRANSFORMATION OF TARTARIC ACID: A FACILE SYNTHESIS OF DERIVATIVES OF OPTICALLY ACTIVE α-HYDRXYOALDEHYDES

Methods for synthesis of (R)- and (S)-2-benzyloxy- and 2-(t-butyldiphenylsilyloxy)-aldehydes from optically active tartaric acids are described.