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Key Documents

698385

Sigma-Aldrich

1,2-Bis[(2S,5S)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate

Synonym(s):

(S,S)-Et-DUPHOS-Rh

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About This Item

Empirical Formula (Hill Notation):
C30H48BF4P2Rh
CAS Number:
Molecular Weight:
660.36
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

form

powder

Quality Level

SMILES string

[Rh+].F[B-](F)(F)F.C1CC=CCCC=C1.CC[C@H]2CC[C@H](CC)P2c3ccccc3P4[C@@H](CC)CC[C@@H]4CC

InChI

1S/C22H36P2.C8H12.BF4.Rh/c1-5-17-13-14-18(6-2)23(17)21-11-9-10-12-22(21)24-19(7-3)15-16-20(24)8-4;1-2-4-6-8-7-5-3-1;2-1(3,4)5;/h9-12,17-20H,5-8,13-16H2,1-4H3;1-2,7-8H,3-6H2;;/q;;-1;+1/b;2-1-,8-7-;;/t17-,18-,19-,20-;;;/m0.../s1

InChI key

DSYBEQKPSKLNMC-ZCTOJWETSA-N

Application

DuPhos and BPE Ligands: Highly Efficient Privileged Ligands

Catalyst for:
  • Preparation of a key unit B precursor of cryptophycins via Horner-Wadsworth-Emmons reaction and asymmetric hydrogenation
  • Preparation of constrained phenylalanine analogs via Heck reaction followed by asymmetric hydrogenation and cyclization steps
  • Enantioselective preparation of N-benzyloxy-β-amino acid Me esters by hydrogenation of α-(benzyloxyaminomethyl)acrylate stereoisomers
  • Preparation of fluoro amino acids as synthons for potent macrocyclic HCV NS3 protease inhibitors
  • Stereoselective preparation of triply isotope-labeled Ser, Cys, and Ala
  • Preparation of β-amino acids from asymmetric hydrogenation of α-(aminomethyl)acrylates
  • Asymmetric hydrogenation of a-primary and secondary amino ketones and asymmetric synthesis of (-)-arbutamine and (-)-denopamine

Legal Information

Sold in collaboration with Kanata Chemical Technologies Inc. for research purposes only. These compounds were made and sold under license from E.I. du Pont de Nemours and Company, which license does not include the right to use the compounds in producing products for sale in the pharmaceutical field.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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