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(1R)-3,3'-bis[3,5-bis(1,1-dimethylethyl)-4-methoxyphenyl]-[1,1'-Binaphthalene]-2,2'-diol, also known as Bisbenzavitriol, is a chiral chemical compound belonging to the binaphthol family. It is characterized by its two chiral centers and typically appears as a white to off-white powder. Bisbenzavitriol is renowned for its role as a chiral auxiliary in asymmetric synthesis, which is pivotal in the construction of intricate organic molecules such as natural products and pharmaceuticals. Its effectiveness in facilitating various asymmetric reactions, including Diels-Alder reactions, aldol reactions, and cycloadditions, has been well-documented. Additionally, Bisbenzavitriol has demonstrated its potential in catalyzing the highly enantioselective addition of diethylzinc to aldehydes, making it a valuable resource in both academic and industrial realms of organic synthesis.

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  • 1353682-93-5 Structure
  • Basic information

    1. Product Name: (1R)-3,3'-bis[3,5-bis(1,1-dimethylethyl)-4-methoxyphenyl]-[1,1'-Binaphthalene]-2,2'-diol
    2. Synonyms: (1R)-3,3'-bis[3,5-bis(1,1-dimethylethyl)-4-methoxyphenyl]-[1,1'-Binaphthalene]-2,2'-diol;(S)-3,3'-Bis(3,5-di-tert-butylphenyl)-[1,1'-binapthalene]-2,2'-diol;(R)-3,3'-Bis[3,5-bis(tert-butyl)-4-methoxyphenyl]-[1,1'- binaphthalene]-2,2'-diol, 99%e.e.
    3. CAS NO:1353682-93-5
    4. Molecular Formula: C48H54O2
    5. Molecular Weight: 662.96
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 1353682-93-5.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 741.0±60.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.086±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. PKA: 8.22±0.50(Predicted)
    10. CAS DataBase Reference: (1R)-3,3'-bis[3,5-bis(1,1-dimethylethyl)-4-methoxyphenyl]-[1,1'-Binaphthalene]-2,2'-diol(CAS DataBase Reference)
    11. NIST Chemistry Reference: (1R)-3,3'-bis[3,5-bis(1,1-dimethylethyl)-4-methoxyphenyl]-[1,1'-Binaphthalene]-2,2'-diol(1353682-93-5)
    12. EPA Substance Registry System: (1R)-3,3'-bis[3,5-bis(1,1-dimethylethyl)-4-methoxyphenyl]-[1,1'-Binaphthalene]-2,2'-diol(1353682-93-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1353682-93-5(Hazardous Substances Data)

1353682-93-5 Usage

Uses

Used in Pharmaceutical Industry:
Bisbenzavitriol serves as a crucial chiral auxiliary in the asymmetric synthesis of pharmaceuticals, enabling the production of complex organic molecules with precise stereochemistry. This is vital for ensuring the desired biological activity and therapeutic efficacy of the resulting drugs.
Used in Academic Research:
In academic settings, Bisbenzavitriol is utilized for its ability to promote a variety of asymmetric reactions, which are fundamental to the synthesis of complex organic molecules. Its role in advancing the understanding of asymmetric synthesis and the development of novel synthetic methods is significant.
Used in Catalyst Development:
Bisbenzavitriol is also employed in the development of catalysts for enantioselective reactions, such as the addition of diethylzinc to aldehydes. Its use in this capacity contributes to the advancement of catalytic technologies and the creation of more efficient and selective chemical processes.
Used in Organic Synthesis:
Widely used in organic synthesis, Bisbenzavitriol aids in the construction of complex organic molecules with high enantioselectivity. This is particularly important in the synthesis of natural products and the development of new pharmaceuticals, where the stereochemistry of the molecules is crucial for their biological activity.

Check Digit Verification of cas no

The CAS Registry Mumber 1353682-93-5 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,3,5,3,6,8 and 2 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1353682-93:
(9*1)+(8*3)+(7*5)+(6*3)+(5*6)+(4*8)+(3*2)+(2*9)+(1*3)=175
175 % 10 = 5
So 1353682-93-5 is a valid CAS Registry Number.

1353682-93-5Downstream Products

1353682-93-5Relevant articles and documents

A Ruthenium/Phosphoramidite-Catalyzed Asymmetric Interrupted Metallo-ene Reaction

Trost, Barry M.,Ryan, Michael C.

supporting information, p. 2981 - 2984 (2016/03/19)

Allylic chlorides prepared from commercially available trans-1,4-dichloro-2-butene were converted to trans-disubstituted 5- and 6-membered ring systems with perfect diastereoselectivity and high enantioselectivity under chiral ruthenium catalysis. These products contain stereodefined secondary and tertiary alcohols that originate from the trapping of an alkylruthenium intermediate with adventitious water. Key to the success of this transformation was the development of a new BINOL-based phosphoramidite ligand containing bulky substitution at its 3- and 3′-positions. As a demonstration of product utility, diastereoselective Friedel-Crafts reactions were performed on the chiral benzylic alcohols in high yield and stereoselectivity.

Copper(I)-catalyzed asymmetric desymmetrization: Synthesis of five-membered-ring compounds containing all-carbon quaternary stereocenters

Aikawa, Kohsuke,Okamoto, Tatsuya,Mikami, Koichi

, p. 10329 - 10332 (2012/07/30)

A highly stereoselective catalytic alkylation sequence for the synthesis of highly functionalized and versatile five-membered-ring compounds bearing all-carbon quaternary stereocenters was developed. Enantioselective desymmetrization of achiral cyclopentene-1,3-diones was thus executed by chiral Cu-phosphoramidite catalysts. A variety of complicated cyclopentane derivatives can be synthesized with excellent stereoselectivities using a low catalyst loading in a one-pot operation.

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