Skip to Content
Merck
CN

520160

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 In to View Organizational & Contract Pricing.

Select a Size

About This Item

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Shi Epoxidation Diketal Catalyst, 98%

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

SMILES string

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

InChI key

IVWWFWFVSWOTLP-RWYTXXIDSA-N

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.)

functional group

ether
ketal
ketone

greener alternative category

, Aligned

Quality Level

100

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

新产品
This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCR2121
MKCN5614
MKCH5091
MKBZ2968V
MKBV1547V

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

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)
Shu, L.; Shi, Y.
Tetrahedron, 57, 5213-5213 (2001)
Wang, Z.-X. et al.
Journal of the American Chemical Society, 119, 11224-11224 (1997)
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