929097-92-7

Basic information

• Product Name: S-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate
• Synonyms: (S)-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 96%;(S)-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl Hydrogen Phosphate,99%e.e.;(11bS)-4-Hydroxy-2,6-bis(triphenylsilyl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin
• CAS NO: 929097-92-7
• Molecular Formula: C56H42O4PSi2
• Molecular Weight: 866.075041
• Mol File: 929097-92-7.mol

Chemical Properties

• Melting Point: 329-335°C
• Appearance: white to light-yellow/solid
• Density: 1.328 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.17±0.20(Predicted)
• CAS DataBase Reference: S-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate(CAS DataBase Reference)
• NIST Chemistry Reference: S-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate(929097-92-7)
• EPA Substance Registry System: S-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate(929097-92-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 929097-92-7(Hazardous Substances Data)

Usage

Uses

Used in Catalyst Applications:
S-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate is used as a catalyst for several chemical reactions, enhancing the efficiency and selectivity of the processes.
Used in the Synthesis of 1,3-Dioxolochroman Skeletons:
In the chemical industry, S-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate is used as a catalyst for the synthesis of 1,3-dioxolochroman skeletons. This application is particularly relevant in the production of complex organic molecules and pharmaceutical intermediates. It facilitates the reaction between 3-methyl-2-vinylindoles and ortho-quinone methides, leading to the formation of the desired skeletons.
Used in the Exo-Selective Cyclization of Mupirocin Methyl Ester:
Another application of S-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate is in the exo-selective cyclization of mupirocin methyl ester. This reaction is crucial for the synthesis of specific types of macrolide antibiotics, which are widely used in the treatment of bacterial infections.
Used in the Kinetic Resolution of Cyclic Aliphatic syn-1,3-Diols:
S-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate also plays a role in the kinetic resolution of cyclic aliphatic syn-1,3-diols. These compounds are valuable building blocks in organic chemistry and are used in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals. The catalytic action of S-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate helps in achieving enantioselective transformations, which are essential for obtaining specific enantiomers with desired biological activities.

Reactions

Chiral phosphoric acid catalyst used for the highly enantioselective Friedel-Crafts reaction of indoles with imines. Chiral phosphoric acid catalyst used for the highly enantioselective Friedel-Crafts reaction of pyrrole derivatives with N-acyl imines. 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). [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. Enantioselective desymmetrization of prochiral allenic diols via cooperative catalysis of Pd(OAc)2 and a chiral phosphoric acid.