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520160

Sigma-Aldrich

Shi Epoxidation Diketal Catalyst

greener alternative

98%

Synonyme(s) :

1,2:4,5-Di-O-isopropylidene-β-D-erythro-2,3-hexodiulo-2,6-pyranose

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About This Item

Formule empirique (notation de Hill):
C12H18O6
Numéro CAS:
18422-53-2
Poids moléculaire :
258.27
Numéro MDL:
MFCD11865369
Code UNSPSC :
12352005
ID de substance PubChem :
24874093
Nomenclature NACRES :
NA.22

Pureté

98%

Activité optique

[α]20/D −120.9°, c = 1 in chloroform

Caractéristiques du produit alternatif plus écologique

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

Pf

102-104 °C (lit.)

Autre catégorie plus écologique

, Aligned

Chaîne SMILES 

CC1(C)O[C@@H]2CO[C@]3(COC(C)(C)O3)C(=O)[C@@H]2O1

InChI

1S/C12H18O6/c1-10(2)15-6-12(18-10)9(13)8-7(5-14-12)16-11(3,4)17-8/h7-8H,5-6H2,1-4H3/t7-,8-,12+/m1/s1

Clé InChI

IVWWFWFVSWOTLP-RWYTXXIDSA-N

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Description générale

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

Highly selective and active organocatalyst for the asymmetric epoxidation of alkenes with hydrogen peroxide. Green epoxidation catalyst of choice according to Glaxo-Smith-Kline's reagent guide.

An Efficient Catalytic Asymmetric Epoxidation Method

Use of an Iridium-Catalyzed Redox-Neutral Alcohol-Amine Coupling on Kilogram Scale for the Synthesis of a GlyT1 Inhibitor
This organocatalyst is able to epoxidize trans alkenes and certain cis alkenes with good to excellent yields and selectivities.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Wang, Z.-X. et al.
Journal of the American Chemical Society, 119, 11224-11224 (1997)
Yian Shi
Accounts of chemical research, 37(8), 488-496 (2004-08-18)
Chiral ketones have been shown to be effective organocatalysts for asymmetric epoxidation of olefins with broad substrate scope. High enantioselectivity has been obtained for a wide variety of trans and trisubstituted olefins, as well as a number of cis olefins
Frohn, M.; Shi, Y.
Synthesis, 1979-1979 (2000)
Tu, Y. et al.
Journal of the American Chemical Society, 118, 9806-9806 (1996)
Shu, L.; Shi, Y.
Tetrahedron, 57, 5213-5213 (2001)
Afficher tous les articles scientifiques apparentés

Articles

Asymmetric Epoxidation Using Shi Catalyst

Catalytic asymmetric epoxidation of alkenes has been the focus of many research efforts over the past two decades, the best known methods probably being those developed by Sharpless and Jacobsen-Katsuki.

Asymmetric Epoxidation Using Shi Catalyst

Catalytic asymmetric epoxidation of alkenes has been the focus of many research efforts over the past two decades, the best known methods probably being those developed by Sharpless and Jacobsen-Katsuki.

Asymmetric Epoxidation Using Shi Catalyst

Catalytic asymmetric epoxidation of alkenes has been the focus of many research efforts over the past two decades, the best known methods probably being those developed by Sharpless and Jacobsen-Katsuki.

Asymmetric Epoxidation Using Shi Catalyst

Catalytic asymmetric epoxidation of alkenes has been the focus of many research efforts over the past two decades, the best known methods probably being those developed by Sharpless and Jacobsen-Katsuki.

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