520160

Sigma-Aldrich

Shi Epoxidation Diketal Catalyst

greener alternative

98%

Synonym(s):
1,2:4,5-Di-O-isopropylidene-β-D-erythro-2,3-hexodiulo-2,6-pyranose
Empirical Formula (Hill Notation):
C12H18O6
CAS Number:
Molecular Weight:
258.27
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

optical activity

[α]20/D −120.9°, c = 1 in chloroform

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

mp

102-104 °C (lit.)

SMILES string

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

InChI key

IVWWFWFVSWOTLP-RWYTXXIDSA-N

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General description

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.

Packaging

5 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Wang, Z.-X. et al.
Journal of the American Chemical Society, 119, 11224-11224 (1997)
Tu, Y. et al.
Journal of the American Chemical Society, 118, 9806-9806 (1996)
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...
Shu, L.; Shi, Y.
Tetrahedron, 57, 5213-5213 (2001)
Frohn, M.; Shi, Y.
Synthesis, 1979-1979 (2000)
Articles
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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