(+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane

Base Information

• Chemical Name: (+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane
• CAS No.: 824395-67-7
• Molecular Formula: C₃₄H₃₆P₂
• Molecular Weight: 506.607
• European Community (EC) Number: 815-836-9
• Nikkaji Number: J2.177.229A
• Mol file: 824395-67-7.mol

Synonyms:824395-67-7;(+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane;1,2-Bis((2S,5S)-2,5-diphenylphospholan-1-yl)ethane;(2S,5S)-1-[2-[(2S,5S)-2,5-diphenylphospholan-1-yl]ethyl]-2,5-diphenylphospholane;(2S,5S)-1-{2-[(2S,5S)-2,5-DIPHENYLPHOSPHOLAN-1-YL]ETHYL}-2,5-DIPHENYLPHOSPHOLANE;1,2-Bis(2S,5S-2,5-diphenylphospholano)ethane;MFCD07369028;(S,S)-Phenyl-BPE;(S,S)-Ph-BPE;SCHEMBL4782105;ZHB39567;AKOS030621896;AS-68623;D83187;1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane;(+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane, kanata purity

Chemical Property of (+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane

Chemical Property:

• Melting Point: 144°C
• Boiling Point: 654.2±55.0 °C(Predicted)
• PSA: 27.18000
• LogP: 10.50300
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Sparingly Soluble (3.2E-5 g/L) (25°C).
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 7
• Exact Mass: 506.22922514
• Heavy Atom Count: 36
• Complexity: 530

Purity/Quality:

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

(+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(P(C1C2=CC=CC=C2)CCP3C(CCC3C4=CC=CC=C4)C5=CC=CC=C5)C6=CC=CC=C6
• Isomeric SMILES: C1C[C@H](P([C@@H]1C2=CC=CC=C2)CCP3[C@@H](CC[C@H]3C4=CC=CC=C4)C5=CC=CC=C5)C6=CC=CC=C6
• Uses: (+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane is a chiral reagent that is used as a catalyst and also as an enantioselective reagent in synthetic chemistry. It is a DuPhos and BPE ligands which are highly efficient privileged ligands. It is a chiral phosphine ligand used in the asymmetric hydrogenation of allylic sulfoxides.

Technology Process of (+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane

There total 7 articles about (+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane 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: 95.0%

1,2-bis[(R,R)-2,5-diphenylphospholano]ethane oxide → (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane (528565-79-9,824395-67-7)

Guidance literature:

With trichlorosilane; N,N-dimethyl-aniline; In toluene; Reagent/catalyst; Inert atmosphere; Reflux;

Reference yield: 92.0%

1,2-bis[(R,R)-2,5-diphenylphospholano]ethane-borane → (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane (528565-79-9,824395-67-7)

Guidance literature:

With tetrafluoroboric acid dimethyl ether complex; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ol0341952

Reference yield: 91.0%

C34H36O2P2 → (+)-1,2-bis((2S,5S)-2,5-diphenylphospholanyl)ethane (824395-67-7)

Guidance literature:

With trichlorosilane; triethylamine; In toluene; Inert atmosphere; Reflux;

upstream raw materials:

(R,R)-(+)-1-hydroxy-1-oxo-2,5-trans-diphenylphospholane

(S,S)-(-)-1-chloro-1-r-oxo-2-c,5-t-diphenylphospholane

(R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane

Downstream raw materials:

rhodium(acac)(R,R-1,2-bis(2,5-diphenylphospholano)ethane)

Refernces

• 1、 Wang, Yi-Ming,Buchwald, Stephen L.. "Enantioselective CuH-Catalyzed Hydroallylation of Vinylarenes". supporting information. p. 5024 - 5027. Retrieved 2016/05/19.