(R,R)-I-PR-DUPHOS

Base Information

• Chemical Name: (R,R)-I-PR-DUPHOS
• CAS No.: 136705-65-2
• Molecular Formula: C26H44P2
• Molecular Weight: 418.583
• Mol file: 136705-65-2.mol

Synonyms:(R,R)-I-PR-DUPHOS;(+)-1,2-BIS((2R,5R)-2,5-DI-I-PROPYLPHOSPHOLANO)BENZENE;(+)-1,2-BIS[(2R,5R)-2,5-DIISOPROPYLPHOSPHOLANO]BENZENE;BisRRdiipropylphospholanobenzene;(+)-1,2-Bis[(2R, 5R)-2,5-diisopropylphospholano]benzene, Kanata purity;(+)-1,2-Bis((2R,5R)-2,5-di-i-propylphospholano)benzene,98+%(R,R)-i-Pr-DUPHOS

Chemical Property of (R,R)-I-PR-DUPHOS

Chemical Property:

• Vapor Pressure: 1.02E-09mmHg at 25°C
• Melting Point: 40°C
• Refractive Index: n20/D 1.5701
• Boiling Point: 502°C at 760 mmHg
• Flash Point: 273.4°C
• PSA: 27.18000
• LogP: 7.58700
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: Insoluble in water.

Purity/Quality:

98%,99%, ^*data from raw suppliers

(+)-1,2-Bis((2R,5R)-2,5-di-i-propylphospholano)benzene, 98+% (R,R)-i-Pr-DUPHOS ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: It is used as ligands like DuPhos and BPE ligands and are highly efficient privileged ligands. DuPhos and BPE Ligands: Highly Efficient Privileged Ligands

Technology Process of (R,R)-I-PR-DUPHOS

There total 3 articles about (R,R)-I-PR-DUPHOS 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:

(3S,6S)-3,6-dihydroxy-2,7-dimethyloctane (129705-30-2) → (-)-1,2-bis[(2R,5R)-2,5-diisoprohylphospholano]benzene (136705-65-2,943848-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) SOCl₂, 2.) RuCl₃*3H₂O, NaIO₄ / 1.) CCl₄, reflux, 1.5 h, 2.) CCl₄, CH₃CN, H₂O, 25 deg C, 1 h

2: 1.) n-BuLi, 3.) n-BuLi

With ruthenium trichloride; sodium periodate; n-butyllithium; thionyl chloride;

Reference yield:

1,2-bis(phosphino)benzene (80510-04-9) + (3S,6S)-3,6-dihydroxy-2,7-dimethyloctane cyclic sulfate (136705-68-5) → (-)-1,2-bis[(2R,5R)-2,5-diisoprohylphospholano]benzene (136705-65-2,943848-50-8)

Guidance literature:

Multistep reaction;

DOI:10.1021/ja00022a047

Reference yield:

[Cu((R,R)-i-Pr-DuPhos)(OSiMe3)]n + PHMe(Is) (158748-69-7) → Cu((R,R)-i-Pr-DuPhos)(PMeIs) + C45H80CuOP3Si + (-)-1,2-bis[(2R,5R)-2,5-diisoprohylphospholano]benzene (136705-65-2,943848-50-8)

Guidance literature:

In tetrahydrofuran; at 20 ℃; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.inorgchem.9b01263

upstream raw materials:

1,2-bis(phosphino)benzene

(3S,6S)-3,6-dihydroxy-2,7-dimethyloctane cyclic sulfate

(3S,6S)-3,6-dihydroxy-2,7-dimethyloctane

PHMe(Is)

Refernces

• 1、 Burk, Mark J.,Feaster, John E.,Nugent, William A.,Harlow, Richard L.. "Preparation and use of C2-symmetric bis(phospholanes): Production of α-amino acid derivatives via highly enantioselective hydrogenation reactions". . p. 10125 - 10138. Retrieved 2007/10/02.