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
• Article Data: 27

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

Chemical Properties

white to light yellow crystal powde

Uses

Hydrogen-bonding organocatalyst examined in terms of acidity, deprotonation enthalpies and hydrogen bondingCatalyst involved in synthesis of cyclopropylamines via addition reactions of Grignard reagents to amidesReactant or reagent involved in:Enantioswitching of catalytic asymmetric hydroborationSynthesis of derivative ligands for asymmetric hydroformylation of alkenesAmide-directed catalytic asymmetric hydroboration of trisubstituted alkenesAddition of deactivated alkyl Grignard reagents to aldehydes

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

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

Downstream Products

• 121471-25-8 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1,4-dimethyl-1H-pyridin-2-one 

Relevant articles and documents

Asymmetric ozone oxidation of silylalkenes using a C2- symmetrical dialkoxysilyl group as a chiral auxiliary

Ozone oxidation of silyl-substituted alkenes, namely silylalkenes, proceeds in an addition-type manner to afford α-silylperoxy carbonyl compounds in good to excellent yields, without the formation of normal ozonolysis products. Herein the ozone oxidation

Chiral Aluminum Complex Controls Enantioselective Nickel-Catalyzed Synthesis of Indenes: C?CN Bond Activation

A chiral aluminum complex controlled, enantioselective nickel-catalyzed domino reaction of aryl nitriles and alkynes proceeding by C?CN bond activation was developed. The reaction provides various indenes, bearing chiral all-carbon quaternary centers, under mild reaction conditions in yields of 32 to 91 percent and ee values within the 73–98 percent range. The reaction mechanism and aspects of stereocontrol were investigated by DFT calculations.

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

Enantioselective vinylation of aldehydes via direct catalytic asymmetric Grignard reaction of aldehdyes and the vinyl Grinard reagent is a long-standing challenge. This work demonstrated that the magnesium (S)-3,3′-dimethyl BINOLate enantioselectively catalyze the direct vinylation of aldehydes with the deactivated vinylmagnesium bromide by bis(2-[N,N′-dimethylamino]ethyl) ether (BDMAEE) in the addition of n-butylmagnesium chloride. The highest ee of 63% was achieved up to date.