S-3,3'-Bis(3,5-bis(methyl)phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate

Base Information

• Chemical Name: S-3,3'-Bis(3,5-bis(methyl)phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate
• CAS No.: 1170736-59-0
• Molecular Formula: C36H30O4P
• Molecular Weight: 557.594761
• Hs Code.: 2809200000
• Mol file: 1170736-59-0.mol

Synonyms:(S)-3,3'-Bis[3,5-dimethylphenyl]-1,1'-binapthyl-2,2'-diyl hydrogenphosphate;(S)-3,3'-Bis(3,5-dimethylphenyl)-1,1'-binaphthyl-2,2'-diyl Hydrogen Phosphate;S-3,3'-Bis(3,5-bis(methyl)phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate;(S)-3,3'-Bis(3,5-dimethylphenyl)-1,1'-binaphthyl-2,2'-diyl Hydrogen Phosphate,99%e.e.;(11bS)-2,6-Bis(3,5-dimethylphenyl)-4-hydroxy-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin;(11bS)-2,6-Bis(3,5-dimethylphenyl)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide;Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin, 2,6-bis(3,5-dimethylphenyl)-4-hydroxy-, 4-oxide, (11bS)-;(11BS)-2,6-BIS(3,5-DIMETHYLPHENYL)-4-HYDROXY-4-OXIDE-DINAPHTHO[2,1-D:1',2'-F][1,3,2]DIOXAPHOSPHEPIN,98%,(99%EE)

Chemical Property of S-3,3'-Bis(3,5-bis(methyl)phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate

Chemical Property:

• Boiling Point: 755.9±70.0 °C(Predicted)
• PKA: 1.11±0.20(Predicted)
• PSA: 65.57000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 10.09920

Purity/Quality:

99% ^*data from raw suppliers

(S)-3,3'-Bis[3,5-dimethylphenyl]-1,1'-binapthyl-2,2'-diyl hydrogenphosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-3,3'-Bis(3,5-bis(methyl)phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate

There total 4 articles about S-3,3'-Bis(3,5-bis(methyl)phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 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: 81.0%

(S)-3,3’-bis(3,5-dimethylphenyl)-[1,1‘-binaphthalene]-2,2’-diol (215433-51-5) → C36H29O4P (1170736-59-0,861909-53-7)

Guidance literature:

(S)-3,3’-bis(3,5-dimethylphenyl)-[1,1‘-binaphthalene]-2,2’-diol; With pyridine; trichlorophosphate; for 5h; Inert atmosphere;

With water; In pyridine; for 0.5h;

DOI:10.1021/ol901114f

Reference yield:

(S)-2,2'-dimethoxy-1,1'-dinaphthyl (75640-87-8) → C36H29O4P (1170736-59-0,861909-53-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: bromine / dichloromethane / 1 h / 0 °C

2.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine; potassium fluoride / tetrahydrofuran / 18 h / Reflux

3.1: boron tribromide / dichloromethane / 1 h / 0 °C

4.1: trichlorophosphate / pyridine / 5 h / Inert atmosphere

4.2: 0.5 h / Inert atmosphere

With potassium fluoride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; bromine; boron tribromide; trichlorophosphate; tricyclohexylphosphine; In tetrahydrofuran; pyridine; dichloromethane; 2.1: |Suzuki Coupling / 3.1: |Suzuki Coupling;

DOI:10.1021/ol5028255

Reference yield:

(S)-3-bromo-1-(3-bromo-2-methoxynaphthalen-1-yl)-2-methoxynaphthalene (75714-60-2) → C36H29O4P (1170736-59-0,861909-53-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine; potassium fluoride / tetrahydrofuran / 18 h / Reflux

2.1: boron tribromide / dichloromethane / 1 h / 0 °C

3.1: trichlorophosphate / pyridine / 5 h / Inert atmosphere

3.2: 0.5 h / Inert atmosphere

With potassium fluoride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; boron tribromide; trichlorophosphate; tricyclohexylphosphine; In tetrahydrofuran; pyridine; dichloromethane; 1.1: |Suzuki Coupling / 2.1: |Suzuki Coupling;

DOI:10.1021/ol5028255

upstream raw materials:

(S)-3,3’-bis(3,5-dimethylphenyl)-[1,1‘-binaphthalene]-2,2’-diol

(S)-2,2'-dimethoxy-1,1'-dinaphthyl

(S)-3-bromo-1-(3-bromo-2-methoxynaphthalen-1-yl)-2-methoxynaphthalene

Refernces

• 1、 Evans,Gestwicki. "Erratum: Enantioselective organocatalytic Hantzsch synthesis of polyhydroquinolines (Organic Letters (2009) 11:14 (2957-2959) DOI: 10.1021/ol901114f)". supporting information. p. 6040 - 6040. Retrieved 2015/01/08.
• 2、 Hatano, Manabu,Ikeno, Takumi,Matsumura, Tokihiko,Torii, Shinobu,Ishihara, Kazuaki. "Chiral lithium salts of phosphoric acids as Lewis acid-base conjugate catalysts for the enantioselective cyanosilylation of ketones". supporting information; experimental part. p. 1776 - 1780. Retrieved 2009/07/01.