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692980

Sigma-Aldrich

(S)-DTBM-SEGPHOS®

≥94%

Synonym(s):

(S)-(+)-5,5′-Bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4′-bi-1,3-benzodioxole

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About This Item

Empirical Formula (Hill Notation):
C74H100O8P2
CAS Number:
210169-40-7
Molecular Weight:
1179.53
MDL number:
MFCD09753003
UNSPSC Code:
12352005
PubChem Substance ID:
329761548
NACRES:
NA.22

Quality Level

100

Assay

≥94%

form

powder

SMILES string

COc1c(cc(cc1C(C)(C)C)P(c2cc(c(OC)c(c2)C(C)(C)C)C(C)(C)C)c3ccc4OCOc4c3-c5c6OCOc6ccc5P(c7cc(c(OC)c(c7)C(C)(C)C)C(C)(C)C)c8cc(c(OC)c(c8)C(C)(C)C)C(C)(C)C)C(C)(C)C

InChI

1S/C74H100O8P2/c1-67(2,3)47-33-43(34-48(61(47)75-25)68(4,5)6)83(44-35-49(69(7,8)9)62(76-26)50(36-44)70(10,11)12)57-31-29-55-65(81-41-79-55)59(57)60-58(32-30-56-66(60)82-42-80-56)84(45-37-51(71(13,14)15)63(77-27)52(38-45)72(16,17)18)46-39-53(73(19,20)21)64(78-28)54(40-46)74(22,23)24/h29-40H,41-42H2,1-28H3

InChI key

ZNORAFJUESSLTM-UHFFFAOYSA-N

Application

Takasago Ligands and Complexes for Asymmetric Reactions
Catalytic ligand for:
  • Enantioselective synthesis of secondary allylic alcohols via enantioselective reductions of α,β-unsaturated ketones
  • Stereoselective preparation of cyclohexanone derivatives via rhodium-catalyzed rearrangement of allyl or allenic cyclobutanols
  • Cu-catalyzed asymmetric conjugate reduction of beta-substituted unsaturated phosphonates to give optically active beta-stereogenic alkylphosphonates
  • Asymmetric synthesis of cyclohexenones via Rh-catalyzed desymmetrization through enantioselective C-C bond activation and ring expansion of allenyl cyclobutanols
  • Enantioselective synthesis and crystal structure of P-stereogenic alkynylphosphine oxides by Rh-catalyzed [2+2+2] cycloaddition

Legal Information

Sold in collaboration with Takasago for research purposes only. JP Registration No. 3148136
SEGPHOS is a registered trademark of Takasago Intl. Corp.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP1236
MKCJ9478
MKCG5528
MKCF0626
MKBZ5489V

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Articles

Takasago Ligands

Hydrogenation, Asymmetric Catalysis, Binap, SEGPHOS®, Aldol reaction, Alkenylation, Arylation, Mannich reaction, Fluorination, Michael addition, Hydrosilylation, Cycloaddition, Takasago

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