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

Description

(+)-Taddol, also known as (1R,2R,4R,5R)-1,2,4,5-tetrahydroxy-2,3,5,6-tetramethylheptan-4-ol, is a chiral, non-racemic, and highly functionalized secondary alcohol. It is a versatile and efficient ligand for asymmetric catalysis, known for its ability to induce high enantioselectivity in various chemical reactions.

Uses

Used in Chemical Synthesis:
(+)-Taddol is used as a ligand for enantioselective Lewis-acid mediated Diels-Alder reactions, allyltitanation of aldehydes, and Michael-Mukaiyama additions promoted by chiral Ti-complexes. Its unique structure and properties enable it to act as a chiral auxiliary, facilitating the formation of enantiomerically pure products with high selectivity.
Used in Pharmaceutical Industry:
(+)-Taddol is used as a chiral building block in the synthesis of pharmaceutical compounds, contributing to the development of enantiomerically pure drugs with improved efficacy and reduced side effects.
Used in Asymmetric Catalysis:
(+)-Taddol is used as a ligand in asymmetric catalysis, enhancing the selectivity and efficiency of various chemical reactions, leading to the production of enantiomerically pure compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

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

• 73346-73-3 (4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 108-86-1 bromobenzene 
• 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 
• 1445-91-6 (S)-1-phenylethanol 
• 1517-69-7 (R)-1-phenylethanol 
• 117803-32-4 [(4S,5S)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione 

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.