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700762 Sigma-Aldrich

(S)-SIPHOS-PE

97%

Synonym: (11aS)-(−)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1′, 7′-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine, N-Di[(R)-1-phenylethyl]-[(S)-1,1′-spirobiindane-7,7′-diyl]-phosphoramidite

  • CAS Number 500997-70-6

  • Empirical Formula (Hill Notation) C33H32NO2P

  • Molecular Weight 505.59

  •  MDL number MFCD08459342

  •  PubChem Substance ID 329762229

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Other Chiral Ligands
Quality Level   100
assay   97%
optical activity   [α]22/D −65.0°, c = 1 in chloroform
mp   120-125 °C
storage temp.   −20°C
SMILES string   C[C@@H](N([C@H](C)c1ccccc1)P2Oc3cccc4CCC5(CCc6cccc(O2)c56)c34)c7ccccc7
InChI   1S/C33H32NO2P/c1-23(25-11-5-3-6-12-25)34(24(2)26-13-7-4-8-14-26)37-35-29-17-9-15-27-19-21-33(31(27)29)22-20-28-16-10-18-30(36-37)32(28)33/h3-18,23-24H,19-22H2,1-2H3/t23-,24-,33?/m1/s1
InChI key   ZXLQLIDJAURBDD-HRPAVAKOSA-N

Description

Application

(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.

Packaging

50, 250 mg in amber glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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