93379-48-7

Basic information

• Product Name: (-)-Taddol
• Synonyms: (4R,5R)-4,5-BIS(DIPHENYLHYDROXYMETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE;(4R,5R)-4,5-BIS(DIPHENYLHYDROXYMETHYL)-2,2-DIMETHYL-DIOXOLANE;(-)-4,5-BIS[HYDROXY(DIPHENYL)METHYL]-2,2-DIMETHYL-1,3-DIOXOLANE;(R,R)-TADDOL;(R,R)-(-)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRAPHENYL-L-THREITOL;(-)-TADDOL;TADDOL;SEEBACH REAGENT
• CAS NO: 93379-48-7
• Molecular Formula: C₃₁H₃₀O₄
• Molecular Weight: 466.57
• Product Categories: chiral;Asymmetric Synthesis;Biochemistry;Dioxanes & Dioxolanes;Dioxolanes;O-Substituted Sugars;Sugar Alcohols;Sugars;Synthetic Organic Chemistry;CHIRAL CHEMICALS;Chiral Oxygen;TADDOL Series
• Mol File: 93379-48-7.mol

Chemical Properties

• Melting Point: 193-195 °C(lit.)
• Boiling Point: 489.39°C (rough estimate)
• Flash Point: 336.7 °C
• Appearance: white/Powder
• Density: 1.0864 (rough estimate)
• Vapor Pressure: 6.69E-17mmHg at 25°C
• Refractive Index: -69 ° (C=1, CHCl3)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 12.28±0.29(Predicted)
• BRN: 3657855
• CAS DataBase Reference: (-)-Taddol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Taddol(93379-48-7)
• EPA Substance Registry System: (-)-Taddol(93379-48-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/38-36/37/38-20/21/22
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 93379-48-7(Hazardous Substances Data)

Usage

Uses

Used in Asymmetric Catalysis:
(-)-Taddol is used as a hydrogen-bonding organocatalyst for various applications in asymmetric catalysis. Its strong hydrogen-bonding ability and chiral structure make it an effective catalyst in promoting enantioselective reactions.
Used in the Synthesis of Cyclopropylamines:
(-)-Taddol is used as a reactant or reagent in the synthesis of cyclopropylamines via addition reactions of Grignard reagents to amides. This process allows for the formation of cyclopropylamines with high enantioselectivity, which are important building blocks in the synthesis of pharmaceuticals and agrochemicals.
Used in Enantioswitching of Catalytic Asymmetric Hydroboration:
(-)-Taddol is employed as a catalyst in the enantioswitching of catalytic asymmetric hydroboration. This process enables the selective formation of one enantiomer over the other, which is crucial for the production of enantiomerically pure compounds.
Used in the Synthesis of Derivative Ligands for Asymmetric Hydroformylation:
(-)-Taddol is used as a reactant or reagent in the synthesis of derivative ligands for asymmetric hydroformylation of alkenes. These ligands play a vital role in enhancing the enantioselectivity and efficiency of the hydroformylation process.
Used in Amide-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes:
(-)-Taddol is utilized as a catalyst in the amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes. This method allows for the selective formation of enantioenriched products, which are valuable intermediates in the synthesis of complex organic molecules.
Used in the Addition of Deactivated Alkyl Grignard Reagents to Aldehydes:
(-)-Taddol is used as a catalyst in the addition of deactivated alkyl Grignard reagents to aldehydes. This process enables the formation of alcohols with high enantioselectivity, which are important for the synthesis of biologically active compounds and pharmaceuticals.

InChI:InChI=1/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

Upstream product

• 108-86-1 bromobenzene 
• 73346-73-3 (4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 37031-29-1 (+)-dimethyl-2,3-O-isopropylidene-D-tartrate 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 100-58-3 phenylmagnesium bromide 
• 77-76-9 2,2-dimethoxy-propane 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 195449-36-6 Pent-4-enoic acid (R)-7-oxo-1-pentyl-heptyl ester 

Downstream Products

• 144109-23-9 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with methanol 
• 147700-62-7 (1R,7R)-9,9-dimethyl-2,2,4,6,6-pentaphenyl-3,5,8,10-tetraoxa-4-phosphabicyclo<5.3.0>decane 
• 351524-90-8 (2R,3R)-1-Hydroxy-{[2,3](2,2-dimethyl)methylenedioxy}-1,1,4,4-tetraphenyl-10-tosyloxy-5,8-dioxadecane 
• 1192678-82-2 (3aR,8aR)-(-)-(2,2-dimethyl-4,4,8,8-tetraphenyl-tetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-yl)dimethylamine 
• 329363-38-4 (3aR,8aR)-2,2-dimethyl-4,4,8,8-tetraphenylperhydro-6λ⁵-[1,3]dioxolo-[4,5-e][1,3,2]dioxaphosphepin-6-one 
• 1565-74-8 (R)-1-phenyl-1-propanol 
• 1517-69-7 (R)-1-phenylethanol 

Relevant articles and documents

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Enantioselective vinylation of aldehydes with the vinyl Grignard reagent catalyzed by magnesium complex of chiral BINOLs

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Based on the chiral diamine spiro skeleton chiral phosphorus nitrile catalyst, preparation method and application thereof

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