CAS 929097-92-7 (S)-(+)-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate, min. 98% [(S)-TiPSY]

Synonyms

(11bS)-4-Hydroxy-2,6-bis(triphenylsilyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine4-oxide; Phosphoric acid (aR)-3,3'-bis(triphenylsilyl)-1,1'-binaphthalene-2,2'-diyl ester; (11bS)-4-Hydroxy-2,6-bis(triphenylsilyl)dinaphtho-[2,1-d1 inverted exclamation marka,2 inverted exclamation markaf]-[1,3,2]-dioxaphosphepin 4-oxide; (S)-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate, 96%; (R)-(-)-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; J-524233; R-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-di; 791616-55-2; (S)-(+)-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate; Phosphoric acid (aS)-3,3'-bis(triphenylsilyl)-1,1'-binaphthalene-2,2'-diyl ester;

IUPAC Name

(13-hydroxy-13-oxo-16-triphenylsilyl-12,14-dioxa-13λ5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-10-yl)-triphenylsilane;

Molecular Weight

865.084g/mol

Molecular Formula

C56H41O4PSi2;

Canonical SMILES

C1=CC=C(C=C1)[Si](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC5=CC=CC=C5C6=C4OP(=O)(OC7=C6C8=CC=CC=C8C=C7[Si](C9=CC=CC=C9)(C1=CC=CC=C1)C1=CC=CC=C1)O;

InChI

InChI=1S/C56H41O4PSi2/c57-61(58)59-55-51(62(43-25-7-1-8-26-43,44-27-9-2-10-28-44)45-29-11-3-12-30-45)39-41-23-19-21-37-49(41)53(55)54-50-38-22-20-24-42(50)40-52(56(54)60-61)63(46-31-13-4-14-32-46,47-33-15-5-16-34-47)48-35-17-6-18-36-48/h1-40H,(H,57,58);

InChI Key

BDQOCXQVIFQJRK-UHFFFAOYSA-N;

Complexity

1320

Covalently-Bonded Unit Count

Exact Mass

864.228g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

864.228g/mol

Rotatable Bond Count

Topological Polar Surface Area

55.8A^2

Application

(S)-(+)-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate, also known as (S)-TiPSY, is a versatile chiral phosphoric acid catalyst designed to facilitate a variety of enantioselective reactions with high precision and efficiency. It plays a crucial role in the synthesis of complex chemical structures, such as 1,3-dioxolochroman skeletons and exo-selective cyclization of mupirocin methyl ester. This catalyst enables the kinetic resolution of cyclic aliphatic syn-1,3-diols, making them highly valuable as building blocks in chemical synthesis. Furthermore, (S)-TiPSY enhances the enantioselectivity of Friedel-Crafts reactions involving indoles, pyrrole derivatives, and imines, as well as the transfer hydrogenation of hydroxylactams, resulting in enantioenriched tetrahydro-β-carbolines with impressive yields and enantiomeric excess. Additionally, it is instrumental in achieving enantiomerically enriched β-amino-α-hydroxy acid derivatives through the three-component reaction of diazo compounds with imines and water, in cooperation with [Rh2(OAc)4]. Finally, it facilitates the enantioselective desymmetrization of prochiral allenic diols through cooperative catalysis with Pd(OAc)2, demonstrating its broad utility and effectiveness in complex organic synthesis.

January 16, 2025

Highly Effective Catalyst for Research Applications

We used (S)-TiPSY in our lab for the kinetic resolution of cyclic diols. The results were impressive, achieving high enantioselectivity and improving our synthesis processes significantly. An invaluable tool for scientific research.