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500997-70-6

500997-70-6 Structure

500997-70-6 Structure
IdentificationBack Directory
[Name]

(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE
[CAS]

500997-70-6
[Synonyms]

(R)-SIPHOS-PE
(S)-SIPHOS-PE
(S)-SIPHOS-PE 97%
(Sa,R,R)-SIPHOS-PE(WS200893)
N-DI[(R)-1-PHENYLETHYL]-[(R)-1,1'-SPIROBIINDANE-7,7'-DIYL]-PHOSPHORAMIDITE
N-DI[(R)-1-PHENYLETHYL]-[(S)-1,1'-SPIROBIINDANE-7,7'-DIYL]-PHOSPHORAMIDITE
N-Di[(R)-1-phenylethyl]-[(S)-1,1'-spirobiindane-7,7'-diyl]-phosphoramidite ,98%
(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE
(11AS)-(-)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1-PHENYLETHYL]AMINE
(11aS)-(-)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine
(11aS)- 10,11,12,13-tetrahydro-N,N-bis[(1R)-1-phenylethyl]-Diindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-aMine
(11aS)-10,11,12,13-Tetrahydro-N,N-bis[(1R)-1-phenylethyl]-diindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-amine,99%e.e.
(11aS)-(-)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine,min.98%(S)-SIPHOS-PE
(11aS)-(-)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1μ, 7μ-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine, N-Di[(R)-1-phenylethyl]-[(S)-1,1μ-spirobiindane-7,7μ-diyl]-phosphoramidite
[Molecular Formula]

C33H32NO2P
[MDL Number]

MFCD08459342
[MOL File]

500997-70-6.mol
[Molecular Weight]

505.59
Chemical PropertiesBack Directory
[Melting point ]

99-101°C
[alpha ]

-63.5° (c 1.0, CH2Cl2)
[Boiling point ]

617.8±65.0 °C(Predicted)
[storage temp. ]

?20°C
[form ]

solid
[pka]

0.40±0.20(Predicted)
[color ]

white
[optical activity]

[α]22/D 65.0°, c = 1 in chloroform
[Sensitive ]

moisture sensitive
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-36/37
[WGK Germany ]

3
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethyl acetate-->Tetrahydrofuran-->PETROLEUM ETHER-->Triethylamine-->Acetone-->n-Butyllithium-->Phosphorus trichloride-->(S)-1,1'-SPIROBIINDANE-7,7'-DIOL-->CALCIUM HYDRIDE-->(R,R)-(+)-BIS(ALPHA-METHYLBENZYL)AMINE HYDROCHLORIDE
Questions And AnswerBack Directory
[Reaction]

  1. Chiral ligands for copper-catalyzed asymmetric allylic alkylation with dialkylzincs.
  2. Chiral ligands for copper-catalyzed asymmetric conjugate addition of diethylzinc to enones.
  3. Chiral ligands for palladium-catalyzed asymmetric hydrosilylation of styrenes
  4. Chiral ligands for copper-catalyzed asymmetric ring-opening of oxabicyclic alkenes with Grignard reagents.
  5. Chiral ligands for nickel-catalyzed asymmetric hydrovinylation of α-alkyl vinylarenes.
  6. Chiral ligands for iridium-catalyzed asymmetric hydrogenation of cyclic enamines.
  7. Chiral ligands for iridium-catalyzed asymmetric hydrogenation of cyclic imines.
  8. Chiral ligands for gold-catalyzed asymmetric [2 + 2] cycloaddition reaction.
  9. Chiral ligands for rhodium-catalyzed asymmetric hydroacylation of salicylaldehydes to homoallylic sulfides.
  10. Chiral ligands for palladium-catalyzed asymmetric carboamination reactions. 
Reactions of 500997-70-6_1
Reactions of 500997-70-6_2
Reactions of 500997-70-6_3
Reactions of 500997-70-6_4
Hazard InformationBack Directory
[Uses]

(S)-SIPHOS-PE is a chiral spiro phosphoramidate ligand that can be used to synthesize:
  • Spiroindolenines by Pd-catalyzed intramolecular dearomative arylation of haloaryl-3-substituted indoles.
  • Enantioselective conjugate addition compound by Cu-catalyzed 1,4-addition of diethylzinc (Et2Zn) to cyclic enones.
  • Octaketide natural products via rhodium-phosphoramidite catalyzed alkene hydroacylation.

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