CAS 56977-92-5 (R,R)-(-)-1,2-Bis[(o-methoxyphenyl)(phenyl)phosphino]ethane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, min. 95%

Synonyms

DTXSID10448656; 56977-92-5; SC-67687; (R,R)-(-)-1,2-bis[(o-methoxyphenyl)(phenyl)phosphino]ethane (1,5-cyclooctadiene) rhodium (I) tetrafluroborate; (1Z,5Z)-cycloocta-1,5-diene,(R)-(2-methoxyphenyl)-[2-[(2-methoxyphenyl)-phenylphosphanyl]ethyl]-phenylphosphane,rhodium,tetrafluoroborate; (R,R)-(-)-1,2-BIS[(O-METHOXYPHENYL)(PHENYL)PHOSPHI; BP-12198;

IUPAC Name

(1Z,5Z)-cycloocta-1,5-diene;(R)-(2-methoxyphenyl)-[2-[(2-methoxyphenyl)-phenylphosphanyl]ethyl]-phenylphosphane;rhodium;tetrafluoroborate;

Molecular Weight

756.371g/mol

Molecular Formula

C36H40BF4O2P2Rh-;

Canonical SMILES

[B-](F)(F)(F)F.COC1=CC=CC=C1P(CCP(C2=CC=CC=C2)C3=CC=CC=C3OC)C4=CC=CC=C4.C1CC=CCCC=C1.[Rh];

InChI

InChI=1S/C28H28O2P2.C8H12.BF4.Rh/c1-29-25-17-9-11-19-27(25)31(23-13-5-3-6-14-23)21-22-32(24-15-7-4-8-16-24)28-20-12-10-18-26(28)30-2;1-2-4-6-8-7-5-3-1;2-1(3,4)5;/h3-20H,21-22H2,1-2H3;1-2,7-8H,3-6H2;;/q;;-1;/b;2-1-,8-7-;;/t31-,32-;;;/m1.../s1;

InChI Key

DCGUTTVLWMBBAX-PFAWBQHYSA-N;

Complexity

563

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Defined Bond Stereocenter Count

Exact Mass

756.159g/mol

Formal Charge

-1

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

756.159g/mol

Rotatable Bond Count

Topological Polar Surface Area

18.5A^2

Application

(R,R)-(-)-1,2-Bis[(o-methoxyphenyl)(phenyl)phosphino]ethane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, an orange crystalline powder with a minimum purity of 95%, serves as a highly efficient catalyst in several key chemical processes. It is utilized in the synthesis of Sinefungin, a nucleoside analog that effectively inhibits the growth of Streptococcus pneumoniae biofilm. Additionally, its derivatives act as inhibitors and structural probes for the enzyme human protein lysine methyltransferase SETD2. Highly reactive and enantioselective, this catalyst is ideal for the asymmetric hydrogenation of various substituted dehydroalanines into N-protected amino acids. It is notably effective in the asymmetric reduction of pentapeptides containing unsaturated phenylalanine or tyrosine linkages into enkephalin, a peptide hormone in the brain. Furthermore, this catalyst is essential for the asymmetric reduction of enol acetates to esters and is used in the preparation of chiral 2-substituted succinic acid derivatives.

February 14, 2025

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