Tetra-O-acetyl-b-D-ribopyranose, CAS:4049-34-7

1,2,3,4-Tetra-O-acetyl-b-D-ribopyranose is a lipase inhibitor that belongs to the class of lipolytic enzymes. It has been shown to be an effective inhibitor of lipases and has demonstrated enantiopure selectivity for the hydrolysis of racemic mixtures. This substance is used in industrial processes as a surrogate for other more expensive substances. The 1,2,3,4-Tetra-O-acetyl-b-D-ribopyranose has been used as a screening tool to identify potential inhibitors of human pancreatic lipase. The results have shown that this compound inhibits the activity of this enzyme with high specificity and sensitivity. Tetra-O-acetyl-beta-D-ribopyranose (TAR) is a carbohydrate derivative that is commonly used in synthetic organic chemistry as a protecting group for various functional groups present in carbohydrates. The acetylation of the hydroxyl groups present in the ribose ring of TAR prevents the reaction of those hydroxyl groups with other reagents, allowing for selective reactions to occur. TAR is also used as an intermediate in the synthesis of other chemicals. Synthesis and Characterization TAR can be synthesized from ribose in a multistep process that involves acetylation of the hydroxyl groups present on the ribose molecule. The synthesis of TAR involves the use of various reagents and catalysts, such as acetic anhydride, acetic acid, and pyridine. The resulting product is then purified and characterized using various techniques, such as nuclear magnetic resonance (NMR) spectroscopy and high-performance liquid chromatography (HPLC). Analytical Methods Various analytical methods can be used to confirm the identity and purity of TAR. These include HPLC, NMR spectroscopy, mass spectrometry (MS), and infrared spectroscopy (IR). Biological Properties TAR is not known to have any biological activity on its own. However, it is commonly used in the synthesis of molecules that have biological activity, such as glycosides. Toxicity and Safety in Scientific Experiments There is limited research available on the toxicity of TAR. However, it is generally considered to be safe for use in scientific experiments when handled and used appropriately. Applications in Scientific Experiments TAR is an important intermediate in the synthesis of various chemicals, including carbohydrates and glycosides. It is also used as a protecting group in the synthesis of many other molecules. Current State of Research There is ongoing research on the synthesis and applications of TAR, particularly in the field of carbohydrate chemistry. Researchers are investigating the use of TAR and other carbohydrate derivatives in the synthesis of new drugs and other biologically active molecules. Potential Implications in Various Fields of Research and Industry The use of TAR in the synthesis of various molecules has potential implications in numerous fields of research, including drug discovery, chemical biology, and materials science. In industry, TAR and other carbohydrate derivatives are used in the production of various products, such as flavors and fragrances. Limitations and Future Directions While TAR has many applications in synthetic organic chemistry, there are limitations to its use. For example, TAR can be difficult to remove from the final product and can interfere with subsequent chemical reactions. Future research may focus on developing new protecting groups that overcome these limitations. Future Directions - Investigating the synthesis and applications of other carbohydrate derivatives as protecting groups. - Developing more efficient methods for removing TAR and other protecting groups from synthesized molecules. - Further research on the use of TAR and other carbohydrates in drug discovery. - Developing new methods for the synthesis of carbohydrates and other glycosides using TAR and other carbohydrate derivatives. - Investigating the use of TAR as a chiral auxiliary in asymmetric synthesis. - Developing new analytical techniques for detecting and characterizing TAR and other carbohydrate derivatives. CAS Number 4049-34-7 Product Name Tetra-O-acetyl-beta-D-ribopyranose IUPAC Name [(3R,4R,5R,6S)-4,5,6-triacetyloxyoxan-3-yl] acetate Molecular Formula C13H18O9 Molecular Weight 318.28 g/mol InChI InChI=1S/C13H18O9/c1-6(14)19-10-5-18-13(22-9(4)17)12(21-8(3)16)11(10)20-7(2)15/h10-13H,5H2,1-4H3/t10-,11-,12-,13+/m1/s1 InChI Key MJOQJPYNENPSSS-LPWJVIDDSA-N SMILES CC(=O)OC1COC(C(C1OC(=O)C)OC(=O)C)OC(=O)C Canonical SMILES CC(=O)OC1COC(C(C1OC(=O)C)OC(=O)C)OC(=O)C Isomeric SMILES CC(=O)O[C@@H]1CO[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C CAS No: 4049-34-7 MDL No: MFCD00006596 Chemical Formula: C13H18O9 Molecular Weight: 318.28