18422-53-2

Basic information

• Product Name: 1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-ERYTHRO-2,3-HEXODIULO-2,6-PYRANOSE
• Synonyms: 1,2:4,5-DI-O-ISOPROPYLIDEN-BETA-ERYTHRO-2,3-HEXODIULO-2,6-PYRANOSE;1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-ERYTHRO-2,3-HEXODIULO-2,6-PYRANOSE;D-EPOXONE;D-EPOXONE(R);1,2:4,5-di-O-isopropylidene-B-D-*erythro-2,3-hexo;D-Epoxone(rg;1,2:4,5-DI-O-ISOPROPYLIDENE-BETA- &;1 2:4 5-DI-O-ISOPROPYLIDENE-B-D-ERYTHRO&
• CAS NO: 18422-53-2
• Molecular Formula: C₁₂H₁₈O₆
• Molecular Weight: 258.27
• Mol File: 18422-53-2.mol

Chemical Properties

• Melting Point: 102-104 °C(lit.)
• Boiling Point: 341.9 °C at 760 mmHg
• Flash Point: 150 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 7.81E-05mmHg at 25°C
• Refractive Index: 1.511
• Storage Temp.: 2-8°C
• Solubility: Soluble in chloroform and methanol.
• BRN: 1319073
• CAS DataBase Reference: 1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-ERYTHRO-2,3-HEXODIULO-2,6-PYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-ERYTHRO-2,3-HEXODIULO-2,6-PYRANOSE(18422-53-2)
• EPA Substance Registry System: 1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-ERYTHRO-2,3-HEXODIULO-2,6-PYRANOSE(18422-53-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 18422-53-2(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Synthesis:
1,2:4,5-Di-O-isopropylidene-beta-D-erythro-2,3-hexodiulo-2,6-pyranose is used as a chemical reagent for the synthesis of Irciniastatin A and B, which are cytotoxic secondary metabolites. These compounds have potential applications in the development of new drugs for the treatment of various diseases, including cancer.
2. Used in Epoxidation Reactions:
1,2:4,5-Di-O-isopropylidene-beta-D-erythro-2,3-hexodiulo-2,6-pyranose serves as a highly selective and active organocatalyst in epoxidation reactions, particularly when using hydrogen peroxide as the oxidizing agent. Its high selectivity and activity make it an ideal choice for green epoxidation processes, which aim to minimize the environmental impact of chemical reactions.
3. Used in Asymmetric Epoxidation:
1,2:4,5-Di-O-isopropylidene-beta-D-erythro-2,3-hexodiulo-2,6-pyranose is used as an efficient catalytic asymmetric epoxidation method, which is crucial for the synthesis of enantiomerically pure compounds. This is particularly important in the pharmaceutical industry, where the stereochemistry of a molecule can significantly impact its biological activity and safety.
4. Used in Green Chemistry:
As a green epoxidation catalyst, 1,2:4,5-Di-O-isopropylidene-beta-D-erythro-2,3-hexodiulo-2,6-pyranose is used to promote environmentally friendly chemical reactions that adhere to the 12 Principles of Greener Chemistry. This includes enhancing catalytic efficiency and reducing waste, making it a preferred choice for sustainable chemical processes.
5. Used in the Synthesis of GlyT1 Inhibitors:
1,2:4,5-Di-O-isopropylidene-beta-D-erythro-2,3-hexodiulo-2,6-pyranose is also employed in the iridium-catalyzed redox-neutral alcohol-amine coupling on a kilogram scale for the synthesis of a GlyT1 inhibitor. GlyT1 inhibitors have potential therapeutic applications in the treatment of various neurological disorders, such as schizophrenia and Alzheimer's disease.

InChI:InChI=1/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

Upstream product

• 25018-67-1 1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 
• 57-48-7 D-Fructose 
• 77-76-9 2,2-dimethoxy-propane 
• 20880-92-6 2,3;4,5-di-O-isopropylidene-β-D-fructopyranose 
• 6347-01-9 fructopyranose 
• 7660-25-5 D-fructose 
• 15080-25-8 C₁₂H₂₀O₆ 

Downstream Products

• 108680-92-8 1,2:4,5-di-O-isopropylidene-3-C-phenyl-β-D-fructopyranose 
• 18422-54-3 1,2;4,5-di-O-isopropylidene-β-D-fructopyranose 
• 187236-00-6 C₂₃H₃₀O₆ 
• 439828-63-4 (5S,8R,9R)-2,2-dimethyl-10-oxo-1,3,6-trioxaspiro[4,5]decane-8,9-diyl diacetate 
• 532394-78-8 3-O-benzoyl-3-C-cyano-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose 
• 532394-80-2 1,2:4,5-di-O-isopropylidene-3-C-(5-phenyl-1,2,4-oxadiazol-3-yl)-β-D-psicopyranose 
• 532394-79-9 3-O-benzoyl-3-C-(N-hydroxycarbamimidoyl)-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose 
• 187236-13-1 (5S,8R,9R,10R)-9-Methoxy-2,2-dimethyl-10-(5-phenyl-pentyl)-1,3,6-trioxa-spiro[4.5]decane-8,10-diol 

Relevant articles and documents

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The present invention relates to an improved process to produce a specific and very efficient epoxidation-catalyst (1,2:4,5-Di-O-isopropylidene-β-D-erythro-2,3-hexodiulo-2,6-pyranose).

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