(-)-Taddol

Base Information

• Chemical Name: (-)-Taddol
• CAS No.: 93379-48-7
• Molecular Formula: C31H30O4
• Molecular Weight: 466.577
• Hs Code.: 29329970
• DSSTox Substance ID: DTXSID30369334
• Nikkaji Number: J231.889J
• Wikidata: Q72509362
• Mol file: 93379-48-7.mol

Synonyms:1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-a,a,a',a'-tetraphenyl-, (4R,5R)- (9CI);1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-a,a,a',a'-tetraphenyl-, (4R-trans)-;(-)-trans-a,a'-(2,2-Dimethyl-1,3-dioxane-4,5-diyl)bis(diphenylmethanol);(2R,3R)-(-)-1,1,4,4-Tetraphenyl-2,3-(2-propylidenedioxy)butane-1,4-diol;(4R,5R)-2,2-Dimethyl-a,a,a',a'-tetraphenyl-1,3-dioxolane-4,5-dimethanol;(R,R)-Taddol;

Chemical Property of (-)-Taddol

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 6.69E-17mmHg at 25°C
• Melting Point: 193-195 °C(lit.)
• Refractive Index: -69 ° (C=1, CHCl3)
• Boiling Point: 633.2 °C at 760 mmHg
• PKA: 12.28±0.29(Predicted)
• Flash Point: 336.7 °C
• PSA: 58.92000
• Density: 1.2 g/cm³
• LogP: 5.37870
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 466.21440943
• Heavy Atom Count: 35
• Complexity: 574

Purity/Quality:

99% ^*data from raw suppliers

2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-L-threitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/38-36/37/38-20/21/22
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC(C(O1)C(C2=CC=CC=C2)(C3=CC=CC=C3)O)C(C4=CC=CC=C4)(C5=CC=CC=C5)O)C
• Isomeric SMILES: CC1(O[C@H]([C@@H](O1)C(C2=CC=CC=C2)(C3=CC=CC=C3)O)C(C4=CC=CC=C4)(C5=CC=CC=C5)O)C
• 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

Technology Process of (-)-Taddol

There total 19 articles about (-)-Taddol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

bromobenzene (108-86-1,52753-63-6) + (-)-dimethy-2,3-O-isopropylidene-L-tartrate (37031-29-1) → (R,R)-TADDOL (93379-48-7)

Guidance literature:

bromobenzene; With n-butyllithium; In diethyl ether; hexane; at 20 ℃; for 2h;

(-)-dimethy-2,3-O-isopropylidene-L-tartrate; In diethyl ether; hexane; at 20 ℃;

DOI:10.1002/ejoc.200400613

Reference yield: 90.0%

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (73346-73-3) + phenylmagnesium bromide → (S,S)-taddol (93222-42-5,93379-48-7,93379-49-8,118139-82-5,126639-52-9,37031-30-4)

Guidance literature:

In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)80147-1

Reference yield: 87.0%

[(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with N,N-dimethyl-2-oxo-2-phenyl-acetamide → N,N-dimethyl-2-oxo-2-phenylacetamide (51579-87-4) + (R,R)-TADDOL (93379-48-7) + (+)-3-hydroxy-1-methyl-3-phenylazetidin-2-one (77184-12-4,115119-00-1,131574-01-1) + (-)-3-hydroxy-1-methyl-3-phenylazetidin-2-one (77184-12-4,115119-00-1,131574-01-1)

Guidance literature:

With cetyltrimethylammonim bromide; In water; for 10h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Irradiation;

DOI:10.1039/c39950001719

upstream raw materials:

(-)-dimethy-2,3-O-isopropylidene-L-tartrate

Pent-4-enoic acid (R)-7-oxo-1-pentyl-heptyl ester

phenylmagnesium bromide

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Downstream raw materials:

[(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with tripropyl-amine

Refernces

Facile synthesis of versatile enantioenriched α-substituted hydroxy esters through a Bronsted acid catalyzed kinetic resolution

10.1021/ol400207t

The research focuses on the efficient synthesis of enantioenriched R-substituted γ-hydroxy esters through a kinetic resolution process catalyzed by a chiral Br?nsted acid. The purpose of this study is to develop a method for producing these versatile and highly valuable molecules, which are important building blocks in the preparation of biological molecules, including natural products and drug candidates. The researchers achieved this by selectively lactonizing bulky racemic esters in the presence of a chiral Br?nsted acid catalyst, leading to the formation of a recoverable enantioenriched hydroxy ester and lactone. The process was found to be scalable and required only low catalyst loadings (0.5 mol %). The study successfully generated all-carbon quaternary centers with high enantioselectivity and demonstrated the versatility of these hydroxy esters by converting them into other synthetically useful materials. Key chemicals used in the process include various chiral Br?nsted acid catalysts, such as TADDOL, thiourea-based acids, camphor sulfonic acid, and BINOL phosphoric acid derivatives, as well as substrates like R-methyl hydroxy tert-butyl ester (()-1a and other ester functionalities.