(-)-2, 3-O-Isopropylidene-D-threitol, CAS:73346-74-4

(-)-2,3-O-Isopropylidene-D-threitol is a chiral compound with two stereoisomers. It is a crystalline solid that melts at 71?C and has a population of 50%. (-)-2,3-O-Isopropylidene-D-threitol is an important intermediate for the synthesis of polyethers with chiral centers. The catalytic asymmetric synthesis of (-)-2,3-O-isopropylidene-D-threitol is achieved by alkylation of (+)-2,3-(dimethoxyphosphinyl)propane with isopropanol. This reaction can be used to produce polyethers with chiral centers in high yields and enantioselectivity.

(-)-2,3-O-Isopropylidene-d-threitol is a compound belonging to the family of sugar alcohols. It is also known as Isoidide or Isodulcite. The compound is a chiral molecule with two enantiomers, namely (-)-Isoidide and (+)-Isoidide. Isoidide is an important chemical compound due to its use in various fields, including medicine, agriculture, and chemical synthesis.

Synthesis and Characterization

There are several methods for the synthesis of (-)-2,3-O-Isopropylidene-d-threitol. One of the most common methods involves the reduction of isoidonic acid, which is obtained from the oxidation of isoidose. The reaction is catalyzed by sodium borohydride or lithium aluminum hydride. Isoidide can also be synthesized by the enzymatic reduction of isoidone using glucose dehydrogenase.

The characterization of (-)-2,3-O-Isopropylidene-d-threitol is typically done through spectroscopic techniques, such as nuclear magnetic resonance (NMR) spectroscopy and infrared (IR) spectroscopy. NMR spectroscopy can provide information about the stereochemistry and purity of the compound, while IR spectroscopy can give information about the functional groups present in the molecule.

Analytical Methods

Several analytical methods have been developed to detect and quantify (-)-2,3-O-Isopropylidene-d-threitol in various matrices. High-performance liquid chromatography (HPLC) coupled with UV-Vis detection is commonly used for the quantification of isoidide in biological and environmental samples. Gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-tandem mass spectrometry (LC-MS/MS) are also used for the analysis of isoidide in complex matrices.

Biological Properties

(-)-2,3-O-Isopropylidene-d-threitol has various biological properties, including anti-inflammatory and antioxidative effects. It has been shown to inhibit the production of nitric oxide in macrophages, which is important in the treatment of inflammatory disorders. Isoidide also exhibits antioxidant activity by scavenging free radicals and preventing lipid peroxidation.

Toxicity and Safety in Scientific Experiments

(-)-2,3-O-Isopropylidene-d-threitol has a low toxicity profile and is not considered toxic to humans and animals at therapeutic doses. However, the safety of isoidide in scientific experiments depends on the solvent and dosage used. Researchers should adhere to standard laboratory safety guidelines when working with Isoidide.

Applications in Scientific Experiments

(-)-2,3-O-Isopropylidene-d-threitol has various applications in scientific experiments. It can be used as a chiral building block in the synthesis of various compounds. Additionally, isoidide can be used as a reducing agent in the synthesis of metallic nanoparticles. Isoidide is also used in the chemical industry as a raw material for the production of various chemicals.

Current State of Research

Currently, research is being conducted to explore the potential therapeutic applications of (-)-2,3-O-Isopropylidene-d-threitol in the treatment of inflammatory disorders and cancer. Additionally, isoidide is being studied for its potential as a green reducing agent in the synthesis of metal nanoparticles.

Potential Implications in Various Fields of Research and Industry

(-)-2,3-O-Isopropylidene-d-threitol has various potential implications in various fields of research and industry. It can be used as a chiral building block in the synthesis of new drugs and chemicals. Additionally, isoidide can be used as a reducing agent in the synthesis of metallic nanoparticles, which have various applications in the field of nanotechnology.

Limitations and Future Directions

One of the biggest limitations of (-)-2,3-O-Isopropylidene-d-threitol is its high cost, which limits its use in large-scale applications. Additionally, the studies on the biological and toxicological properties of isoidide are limited, and more research is needed to fully understand its potential applications.

Future Directions:

1. Development of cost-effective synthesis methods for (-)-2,3-O-Isopropylidene-d-threitol

2. Exploration of the potential of isoidide as a green reducing agent in the synthesis of metallic nanoparticles

3. Study of the potential therapeutic applications of isoidide in the treatment of inflammatory disorders and cancer

4. Development of new analytical methods for the detection and quantification of isoidide in complex matrices

5. Exploration of the potential of isoidide as a chiral building block in the synthesis of new drugs and chemicals

6. Investigation into the toxicological properties of (-)-2,3-O-Isopropylidene-d-threitol

7. Development of new methodologies for the study of the biological properties of isoidide.