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29524

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine]

Name: (<I>R</I>)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-di-<I>tert</I>-butylphenyl)phosphine]
Brand: ALDRICH

≥97%, optical purity ee: ≥99%

Synonym(s):

(R)-2,2′-Bis[bis(3,5-di-tert-butyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl, (R)-3,5-t-Bu-MeOBIPHEP, SL-A121-1

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About This Item

Empirical Formula (Hill Notation):

C₇₀H₉₆O₂P₂

CAS Number:

192138-05-9

Molecular Weight:

1031.46

MDL number:

MFCD09753001

UNSPSC Code:

12352112

PubChem Substance ID:

329753371

NACRES:

NA.22

Quality Level

100

Assay

≥97%

optical purity

ee: ≥99%

SMILES string

COc1cccc(P(c2cc(cc(c2)C(C)(C)C)C(C)(C)C)c3cc(cc(c3)C(C)(C)C)C(C)(C)C)c1-c4c(OC)cccc4P(c5cc(cc(c5)C(C)(C)C)C(C)(C)C)c6cc(cc(c6)C(C)(C)C)C(C)(C)C

InChI

1S/C70H96O2P2/c1-63(2,3)45-33-46(64(4,5)6)38-53(37-45)73(54-39-47(65(7,8)9)34-48(40-54)66(10,11)12)59-31-27-29-57(71-25)61(59)62-58(72-26)30-28-32-60(62)74(55-41-49(67(13,14)15)35-50(42-55)68(16,17)18)56-43-51(69(19,20)21)36-52(44-56)70(22,23)24/h27-44H,1-26H3

InChI key

PBYRAYONARLAQJ-UHFFFAOYSA-N

Related Categories

Chiral Catalysts & Ligands

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General description

sold in collaboration with Solvias AG

Application

Atropisomeric MeOBIPHEP ligands

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] can be used as a ligand to prepare:

1,2-Dihydropyridines through Rh-catalyzed cycloaddition of diynes to sulfonimines.
Enantiorich disubstituted γ-lactams via intramolecular allylic alkylation reaction using Pd catalyst.
A Ru-metal complex, which acts as a hydrogenation catalyst applicable in the synthesis of an organic building block (S)-3-fluoromethyl-γ-butyrolactone.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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Enantioselective γ-lactam synthesis via palladium-catalyzed intramolecular asymmetric allylic alkylation

Bantreil X, et al.

Synlett, 2009(09), 1441-1444 (2009)

Highly enantioselective rhodium-catalyzed [2+2+2] cycloaddition of diynes to sulfonimines

Amatore M, et al.

Journal of the American Chemical Society, 135(12), 4576-4579 (2013)

Development of a scalable synthesis of (S)-3-fluoromethyl-γ-butyrolactone, building block for Carmegliptin′s lactam moiety

Adam J-M, et al.

Organic Process Research & Development, 15(3), 515-526 (2011)

Articles

MeOBIPHEP

Solvias MeOBIPHEP Ligands: State-of-the-art atropisomeric MeOBIPHEP ligands, also referred to as MeO-BIPHEP, originally developed by Roche, have an extraordinarily broad performance profile for many synthetic applications due to their modular ligand design.

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