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700762

(S)-SIPHOS-PE

Name: (<I>S</I>)-SIPHOS-PE
Brand: ALDRICH

97%

Synonym(s):

(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

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About This Item

Empirical Formula (Hill Notation):

C₃₃H₃₂NO₂P

CAS Number:

500997-70-6

Molecular Weight:

505.59

NACRES:

NA.22

PubChem Substance ID:

329762229

UNSPSC Code:

12352005

MDL number:

MFCD08459342

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Properties

Quality Level

100

assay

97%

form

powder

optical activity

[α]22/D −65.0°, c = 1 in chloroform

mp

120-125 °C

functional group

amine, phenyl

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.

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P305 + P351 + P338

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to enones using chiral spiro phosphoramidites as ligands

Zhou H, et al.

The Journal of Organic Chemistry, 68(4), 1582-1584 (2003)

Palladium (0)-catalyzed dearomative arylation of indoles: convenient access to spiroindolenine derivatives

Wu K-J, et al.

Organic Letters, 14(14), 3772-3775 (2012)

Rhodium-phosphoramidite catalyzed alkene hydroacylation: Mechanism and octaketide natural product synthesis

von Delius M, et al.

Journal of the American Chemical Society, 134(36), 15022-15032 (2012)

Global Trade Item Number

SKU	GTIN
700762-50MG	04061833565056
700762-250MG	04061833565049