S-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate Chemical Properties

Melting point:

329-335°C

alpha 

+210° (c=1.0, CHCl3)

Density 

1.32±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

1.17±0.20(Predicted)

form 

solid

color 

white to light-yellow

optical activity

[α]22/D +210°, c = 1 in chloroform

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37

WGK Germany 

3

HS Code 

29319090

S-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate Usage And Synthesis

Chemical Properties

Solid

Uses

(S)-3,3′-Bis(triphenylsilyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate can be used as a catalyst:

• In the synthesis of 1,3-dioxolochroman skeletons by reacting 3-methyl-2-vinylindoles with ortho-quinone methides.
• In the exo-selective cyclization of mupirocin methyl ester.
• In the kinetic resolution of cyclic aliphatic syn-1,3-diols, which are used as valuable building blocks.

Reactions

1. Chiral phosphoric acid catalyst used for the highly enantioselective Friedel-Crafts reaction of indoles with imines.
2. Chiral phosphoric acid catalyst used for the highly enantioselective Friedel-Crafts reaction of pyrrole derivatives with N-acyl imines.
3. Chiral phosphoric acid catalyst used for the enantioselective transfer hydrogenation of hydroxylactams providing enantioenriched tetrahydro-β-carbolines (in dioxane) at room temperature (up to 94% yield, 90% ee).
4. [Rh2(OAc)4]/chiral phosphoric acid catalyst used for the enantioselective symmetric, three-component reaction of diazo compounds with imines and water yielding β-amino-α-hydroxy acid derivatives.
5. Enantioselective desymmetrization of prochiral allenic diols via cooperative catalysis of Pd(OAc)2 and a chiral phosphoric acid.

S-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate(929097-92-7)Related Product Information

• (S)-3,3'-Bis(3,5-diphenyl)phenyl-1,1'-binaphthyl-2,2'-diyl Hydrogen Phosphate
• S-4-oxide-4-hydroxy-2,6-di-1-naphthalenyl-Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin
• S-3,3'-Bis(4-(1,1-diMethylethyl)phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate
• (R)-3,3'-BIS(3,5-BIS(TRIFLUOROMETHYL)PH&
• R-4-oxide-4-hydroxy-2,6-bis[4-(trifluoroMethyl)phenyl]-Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin
• R- 4-oxide-4-hydroxy-2,6-bis([1,1':3',1''-terphenyl]-5'-yl)-Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin
• R-3,3'-Bis(4-(1,1-diMethylethyl)phenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate
• S-3,3'-Bis(triphenylsilyl)-5,5',6,6',7,7',8,8'-Octahydro-1,1'-bi-2-naphthyl phosphate
• S-5,5',6,6',7,7',8,8'-octahydro-3,3'-diphenyl-[1,1'-Binaphthalene]-2,2'-diol
• R-5,5',6,6',7,7',8,8'-Octahydro-1,1'-bi-2-naphthyl phosphate
• (S)-(-)-3,3μ-Bis(triphenylsilyl)-1,1μ-bi-2-naphthol
• (S)-3,3'-Di(anthracen-9-yl)-1,1'-binaphthalene-2,2'-diol
• (S)-(+)-3,3'-BIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-1,1'-BINAPHTHYL-2,2'-DIYL HYDROGENPHOSPHATE, 95%
• S-3,3'-bis[4-(2-naphthalenyl)phenyl]-1,1'-Binaphthalene]-2,2'-diol
• S- 4-oxide--hydroxy-2,6-bis[4-(2-naphthalenyl)phenyl]-Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin
• S-3,3'-Bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate
• (S)-(-)-3,3'-BIS(3,5-BIS(TRIFLUOROMETHY&
• S-4-oxide-4-hydroxy-2,6-bis(4-nitrophenyl)- Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin