93379-49-8

Basic information

• Product Name: (+)-Taddol
• Synonyms: (+)-4,5-BIS[HYDROXY(DIPHENYL)METHYL]-2,2-DIMETHYL-1,3-DIOXOLANE;(4S,5S)-2,2-DIMETHYL-ALPHA,ALPHA,ALPHA',ALPHA'-TETRAPHENYLDIOXOLANE-4,5-DIMETHANOL;(4S,5S)-4,5-BIS(DIPHENYLHYDROXYMETHYL)-2,2-DIMETHYL-DIOXOLANE;(+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRAPHENYL-D-THREITOL;(2S,3S)-(+)-1,1,4,4-TETRAPHENYL-2,3-(2-PROPYLIDENEDIOXY)-BUTANE-1,4-DIOL;(2S,3S)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRAPHENYL-1,2,3,4-BUTANETETROL;(2S,3S)-(+)-4,5-BIS(DIPHENYLHYDROXYMETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE;(+)-TADDOL
• CAS NO: 93379-49-8
• Molecular Formula: C₃₁H₃₀O₄
• Molecular Weight: 466.57
• Product Categories: chiral;Asymmetric Synthesis;Dioxanes & Dioxolanes;Dioxolanes;Synthetic Organic Chemistry;TADDOL Series;Chiral Oxygen
• Mol File: 93379-49-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 193-196 °C(lit.)
• Boiling Point: 633.2 °C at 760 mmHg
• Flash Point: 336.7 °C
• Appearance: white to light yellow crystal powder
• Density: 1.2 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 12.28±0.29(Predicted)
• BRN: 4724097
• CAS DataBase Reference: (+)-Taddol(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Taddol(93379-49-8)
• EPA Substance Registry System: (+)-Taddol(93379-49-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 93379-49-8(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Ligand for enantioselective Lewis-acid mediated Diels-Alder, allyltitanation of aldehydes, and Michael-Mukaiyama additions promoted by chiral Ti-complexes.

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-/m0/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 

Downstream Products

• 121463-31-8 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1-methyl-1H-pyridin-2-one 
• 121463-33-0 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1,5-dimethyl-1H-pyridin-2-one 
• 121463-32-9 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1,6-dimethyl-1H-pyridin-2-one 
• 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 
• 121463-34-1 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 4-methoxy-1-methyl-1H-pyridin-2-one 
• 117859-43-5 [(4S,5S)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 7a-methyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione 
• 117780-11-7 [(4S,5S)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1,4,5,6,7,7a-hexahydro-inden-2-one 
• 117859-41-3 [(4S,5S)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 117780-13-9 [(4S,5S)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 4a-ethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 121463-35-2 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 4-ethoxy-1-methyl-1H-pyridin-2-one 
• 1400792-92-8 (4S,5S)-4-[(chloro)(diphenyl)methyl]-5-[(methoxy)(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane 
• 1400792-91-7 (4S,5S)-5-[(methoxy)(diphenyl)methyl]-2,2-dimethyl-α,α-diphenyl-1,3-dioxolane-4-methanol 
• 138589-30-7 (4S,5S)-5-[(diphenyl)(sulfanyl)methyl]-2,2-dimethyl-a,a-diphenyl-1,3-dioxolane-4-methanol 
• 1400792-93-9 (4S,5S)-5-[(methoxy)(diphenyl)methyl]-2,2-dimethyl-α,α-diphenyl-1,3-dioxolane-4-methanethiol 

Relevant articles and documents

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.

Ni-Al Bimetallic Catalyzed Enantioselective Cycloaddition of Cyclopropyl Carboxamide with Alkyne

A Ni-Al bimetallic catalyzed enantioselective cycloaddition reaction of cyclopropyl carboxamides with alkynes has been developed. A series of cyclopentenyl carboxamides were obtained in up to 99% yield and 94% ee. The bifunctional-ligand-enabled bimetallic catalysis proved to be an efficient strategy for the C-C bond cleavage of unreactive cyclopropanes.

DESIGN OF A NEW CHIRAL HOST COMPOUND, TRANS-4,5-BIS(HYDROXYDIPHENYLMETHYL)-2,2-DIMETHYL-1,3-DIOXACYCLOPENTANE. AN EFFECTIVE OPTICAL RESOLUTION OF BICYCLIC ENONES THROUGH HOST-GUEST COMPLEX FORMATION

The title chiral host compound which was derived from tartaric acid was found to be effective for optical resolution of bicyclic enones through complex formation between them.