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474606

Sigma-Aldrich

(S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II)

Synonym(s):

(S,S)-Co(salen), (S,S)-Jacobsen HKR catalyst

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About This Item

Linear Formula:
[[[(CH3)3C]2C6H2-2-(O-)CH=N]2C6H10]Co
CAS Number:
188264-84-8
Molecular Weight:
603.74
MDL number:
MFCD01631278
UNSPSC Code:
12352001
PubChem Substance ID:
24871025
NACRES:
NA.22

mp

>350 °C (lit.)

Quality Level

200

SMILES string

CC(C)(C)c1cc2C=[N@@H]3[C@H]4CCCC[C@@H]4[N@H]5=Cc6cc(cc(c6O[Co]35Oc2c(c1)C(C)(C)C)C(C)(C)C)C(C)(C)C

InChI

1S/C36H54N2O2.Co/c1-33(2,3)25-17-23(31(39)27(19-25)35(7,8)9)21-37-29-15-13-14-16-30(29)38-22-24-18-26(34(4,5)6)20-28(32(24)40)36(10,11)12;/h17-22,29-30,39-40H,13-16H2,1-12H3;/q;+2/p-2/b37-21+,38-22+;/t29-,30-;/m0./s1

InChI key

ZFWPDJKMASHRPT-IKKUFEJKSA-L

Application

(S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) may be used as a catalyst for the Jacobsen′s hydrolytic kinetic resolution of racemic epoxides, which is a key step during the multi-step synthesis of (+)-patulolide C, macrosphelides(I and G), (-)-(3S,6R)-3,6-dihydroxy-10-methylundecanoic acid, dodoneine, epidodoneine and protein kinase C epsilon (PKCe) inhibitors.
Catalyst for the hydrolytic kinetic resolution of terminal epoxides and the enantioselective ring opening of meso epoxides.

Legal Information

Sold under license from Sterling Pharma Solutions Limited.

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
BCCH8963
BCBV0526
BCBL7635V
BCBJ1419V
BCBF3542V

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RCM mediated synthesis of macrosphelides I and G.
Sharma GVM, and Babu KV.
Tetrahedron Asymmetry, 18(18), 2175-2184 (2007)
The enantioselective Diels-Alder reaction of 1-methoxybuta-1, 3-diene with n-butyl glyoxylate catalyzed by the (salen) Cr (III) Cl and Co (II) complexes.
Kwiatkowski P, et al.
Tetrahedron Asymmetry, 15(20), 3189-3194 (2004)
Strategies for the modulation of phase II metabolism in a series of PKCe inhibitors.
Clemens JJ, et al.
Bioorganic & Medicinal Chemistry Letters, 24(15), 3398-3402 (2014)
A Concise Synthesis of (-)-(3S, 6R)-3, 6-Dihydroxy-10-methylundecanoic Acid Using a Cross-Metathesis Approach.
Sabitha G, et al.
Synthesis, 2010(07), 1217-1222 (2010)
Jacobsen, E.N. et al.
Tetrahedron Letters, 38, 773-773 (1997)
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