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665460

Sigma-Aldrich

(3aR,8aR)-(−)-(2,2-Dimethyl-4,4,8,8-tetraphenyl-tetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-yl)dimethylamine

96%

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About This Item

Empirical Formula (Hill Notation):
C33H34NO4P
CAS Number:
213843-90-4
Molecular Weight:
539.60
MDL number:
MFCD04117685
UNSPSC Code:
12352005
PubChem Substance ID:
24884738
NACRES:
NA.22

Quality Level

100

Assay

96%

form

solid

mp

218-221 °C

functional group

amine
ether
ketal
phenyl

SMILES string

CN(C)P1OC([C@@H]2OC(C)(C)O[C@H]2C(O1)(c3ccccc3)c4ccccc4)(c5ccccc5)c6ccccc6

InChI

1S/C33H34NO4P/c1-31(2)35-29-30(36-31)33(27-21-13-7-14-22-27,28-23-15-8-16-24-28)38-39(34(3)4)37-32(29,25-17-9-5-10-18-25)26-19-11-6-12-20-26/h5-24,29-30H,1-4H3/t29-,30-/m1/s1

InChI key

DRPNADVMTMEWQY-LOYHVIPDSA-N

Application

DSM MonoPhos Family of Highly Efficient Privileged Ligands
Phosphoramidite ligand employed in an asymmetric, iridium-catalyzed, allylic allylation of propenylboronates. Also used in a copper-catalyzed asymmetric conjugate addition of diethylzinc to α,β-unsaturated imines derived from amino acids.

Legal Information

Sold under license from DSM for research purposes only.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
01403CE

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(S)-SIPHOS-PE 97%

Sigma-Aldrich

700762

(S)-SIPHOS-PE

Tetrahedron Letters, 48, 3305-3305 (2007)
Francisco Palacios et al.
Organic letters, 8(23), 5405-5408 (2006-11-03)
[Structure: see text] A highly enantioselective synthesis of alpha-dehydroaminoacids with a stereogenic center in the gamma position through copper-catalyzed asymmetric conjugate addition of diethylzinc to alpha,beta-unsaturated imines using a TADDOL-derived phosphoramidite complex is reported.

Articles

DSM MonoPhos Family

A diverse array of these chiral, monodentate phosphoramidites based on the privileged BINOL platform. The MonoPhos™ family has exhibited high levels of enantiocontrol in synthetic transformations ranging from metal-catalyzed asymmetric 1,4-additions of organometallic reagents to allylic alkylations to desymmetrization of meso-cycloalkene oxides.

DSM MonoPhos™ Ligands

DSM MonoPhos™ Ligands

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