Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

View All Documentation

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C12H18O6
CAS Number:
18422-53-2
Molecular Weight:
258.27
MDL number:
MFCD11865369
UNSPSC Code:
12352005
PubChem Substance ID:
24874093
NACRES:
NA.22

Quality Level

100

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.

sustainability

Greener Alternative Product

mp

102-104 °C (lit.)

greener alternative category

, Aligned

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

Looking for similar products? Visit Product Comparison Guide

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCN5614
MKCH5091
MKBZ2968V
MKBV1547V
MKBW4381V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 3

1 of 3

AD-mix-β

Sigma-Aldrich

392766

AD-mix-β

D-(−)-Fructose ≥99% (HPLC)

Sigma-Aldrich

F0127

D-(−)-Fructose

Grubbs Catalyst® M204 Umicore

Sigma-Aldrich

569747

Grubbs Catalyst® M204

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

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service