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29524

Sigma-Aldrich

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

≥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

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.

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

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)
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)
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)

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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