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  • 718653 - 1,2:4,5-Bis-O-(isopropylidene)-β-L-erythro-2,3-hexodiulo-2,6-pyranose

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718653 Sigma-Aldrich

1,2:4,5-Bis-O-(isopropylidene)-β-L-erythro-2,3-hexodiulo-2,6-pyranose

Synonym: Shi epoxidation catalyst enantiomer

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Epoxidation
optical activity   [α]22/D +111.0°, c = 0.5 in chloroform
mp   98-104 °C
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+/m0/s1
InChI key   IVWWFWFVSWOTLP-YVZVNANGSA-N

Description

Application

Reactant for:
• Diastereoselective synthesis of a-tocopherol via Shi epoxidation
• Synthesis of benzimidazole-based analogs of epothilone A with anticancer activity

Catalyst for:
• Preparation of microtubule-stabilizing and antitumor active analogs of epothilone
• Synthesis of (+)-aurilol via regio- and stereocontrolled A-D ether ring formations

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
1

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Shi Catalyst Asymmetric Epoxidation

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 Sharpless1 and Jacobsen-Kat...
Daniel Weibel
Aldrich ChemFiles 2010, 10.3, 5.
Keywords: Asymmetric synthesis, Catalysis, Epoxidations, Ligands, Methods, Oxidations, Reductions, Shi Epoxidation

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