Basic information Reaction Safety Supplier Related

(S)-(+)-5,5'-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DTBM-SEGPHOS

Basic information Reaction Safety Supplier Related

(S)-(+)-5,5'-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DTBM-SEGPHOS Basic information

Product Name:
(S)-(+)-5,5'-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DTBM-SEGPHOS
Synonyms:
  • (S)-(+)-5,5'-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DTBM-SEGPHOS
  • (S)-(+)-5,5μ-Bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4μ-bi-1,3-benzodioxole
  • (S)-DTBM-SEGPHOS(R)
  • (S)-DTBM-SEGPHOS
  • (S)-5,5'-Bis[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4'-bibenzodioxole
  • (S)-DTBM-SEGPHOS(R) >=94%
  • Phosphine,[(4S)-[4,4'-bi-1,3-benzodioxole]-5,5'-diyl]bis[bis[3,5-bis(1,1-diMethylethyl)-4-Methoxyphenyl]-
  • (S)-(+)-5,5'-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-4,4'-bi-1,3-benzodioxole, min. 98%
CAS:
210169-40-7
MF:
C74H100O8P2
MW:
1179.53
Product Categories:
  • Chiral Phosphine
  • Segphos Series
Mol File:
210169-40-7.mol
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(S)-(+)-5,5'-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DTBM-SEGPHOS Chemical Properties

Melting point:
126-128°C
Boiling point:
987.3±65.0 °C(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
form 
Powder
color 
off-white
CAS DataBase Reference
210169-40-7
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Safety Information

WGK Germany 
3
HS Code 
2932.99.7000
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(S)-(+)-5,5'-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DTBM-SEGPHOS Usage And Synthesis

Reaction

  1. Biaryl bisphosphine ligand with narrow dihedral angle. The DTBM SEGPHOS® ligand, as the ruthenium complex, gives superior enantioselectivity and diastereoselectivity through dynamic kinetic resolution in the asymmetric hydrogenation of a-substituted-β-ketoesters useful in the synthesis of carbapenum antibiotics.
  2. With rhodium, preferential enantioselective hydrogenation of more reactive olefin of extended enone structure.
  3. Rhodium catalyzed chemo-, regio, and entantioselective [2 + 2 + 2] cycloaddition of alkynes with isocyanates.
  4. With copper, enantioselective cross Aldol-type reaction of acetonitrile.
  5. With copper, enantioselective vinylsilane alkenylation of aldehydes.
  6. Gold carbene mediated stereoselective cyclopropanation of propargyl esters.
  7. With copper, enantioselective 1,2-reduction of ketones, and 1,4-reduction of a α,β-usaturated esters.
  8. With copper, catalytic enantioselective Mannich-type reaction.
  9. Enantioselective fluorination of b β-keto esters, tert-butoxycarbonyl lactones and lactmes with Sodeoka's Pd-aqua complex and a fluorinating reagent.
  10. Rh-catalyzed intramolecular olefin or carbonyl hydroacylation.


Uses

Catalytic ligand for:

  • Enantioselective synthesis of secondary allylic alcohols via enantioselective reductions of α,β-unsaturated ketones
  • Stereoselective preparation of cyclohexanone derivatives via rhodium-catalyzed rearrangement of allyl or allenic cyclobutanols
  • Cu-catalyzed asymmetric conjugate reduction of beta-substituted unsaturated phosphonates to give optically active beta-stereogenic alkylphosphonates
  • Asymmetric synthesis of cyclohexenones via Rh-catalyzed desymmetrization through enantioselective C-C bond activation and ring expansion of allenyl cyclobutanols
  • Enantioselective synthesis and crystal structure of P-stereogenic alkynylphosphine oxides by Rh-catalyzed [2+2+2] cycloaddition

(S)-(+)-5,5'-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DTBM-SEGPHOSSupplier

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