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700770

Sigma-Aldrich

(R)-SIPHOS-PE

97%

Synonym(s):

(11aR)-(+)-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]-[(R)-1,1′-spirobiindane-7,7′-diyl]-phosphoramidite

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About This Item

Empirical Formula (Hill Notation):
C33H32NO2P
CAS Number:
500997-69-3
Molecular Weight:
505.59
MDL number:
MFCD08459342
UNSPSC Code:
12352005
PubChem Substance ID:
329762230

assay

97%

form

powder

optical activity

[α]22/D +337°, c = 1 in chloroform

mp

90-96 °C

storage temp.

−20°C

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

Application

(R)-SIPHOS-PE can be used as:
  • A catalyst in the preparation of tricyclic alkaloid (+)-aphanorphine via asymmetric carboamination and Friedel−Crafts reaction.
  • A ligand in the synthesis of chiral ketones via hydroacylation of olefins using salicylaldehyde derivatives.
  • A ligand in the enantioselective synthesis of substituted pyrrolidine derivatives via Pd-catalyzed alkene aminoarylation reactions.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Regio-and enantioselective intermolecular hydroacylation: Substrate-directed addition of salicylaldehydes to homoallylic sulfides
Coulter MM, et al.
Journal of the American Chemical Society, 132(46), 16330-16333 (2010)
Recent developments in palladium-catalyzed alkene aminoarylation reactions for the synthesis of nitrogen heterocycles
Schultz DM and Wolfe JP
Synthesis, 44(03), 351-361 (2012)
Enantioconvergent synthesis of (+)-aphanorphine via asymmetric Pd-catalyzed alkene carboamination
Mai DN, et al.
Organic Letters, 13(11), 2932-2935 (2011)

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