Di-O-isopropylidene-?-D-fructopyranose, CAS:20880-92-6

2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose, 2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose (IDFP) is a natural compound that has been shown to have pharmacological properties. It is an inhibitor of the enzyme alpha-glucosidase and may be used as a treatment for diabetes mellitus type II. IDFP binds to the active site of the enzyme ?-glucosidase, preventing access of the substrate glucose. This causes a decrease in blood glucose levels and has also been shown to reduce cholesterol levels in mice. IDFP is synthesized by reacting ethylene diamine with 2,3:4,5-di-O-isopropylidene b -D -fructofuranose. This reaction produces a heterocycle that undergoes asymmetric synthesis using sodium hydroxide solution and hydrogen fluoride as catalysts.2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose (DIFP) is a cyclic acetal derivative of fructose that has been reported to exhibit a wide range of biological and chemical properties. DIFP has been studied extensively in recent years, and researchers have found that it has significant applications in various scientific fields, including organic chemistry, biochemistry, and pharmacology. This paper aims to provide a comprehensive overview of DIFP, including its definition, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, and limitations and future directions.Synthesis and Characterization DIFP can be synthesized using different methods, including the reaction of fructose with isopropylidene under acidic conditions or the selective acetalization of fructose with isopropylidene in the presence of boron trifluoride etherate or p-toluenesulfonic acid (3). DIFP can be characterized using different techniques, including Nuclear Magnetic Resonance (NMR) spectroscopy, Infrared spectroscopy (IR), and Mass Spectrometry (MS).Analytical Methods DIFP can be analyzed using various analytical methods, including Thin-Layer Chromatography (TLC), High-Performance Liquid Chromatography (HPLC), and Gas Chromatography-Mass Spectrometry (GC-MS). These methods are widely utilized for the qualitative and quantitative analysis of DIFP.Biological Properties DIFP has been found to exhibit a range of biological properties, including antiviral, antitumor, and antidiabetic activities. It has also been reported to exhibit anti-inflammatory properties (4). DIFP has been utilized as a chiral auxiliary in the synthesis of complex molecules due to its high stereochemical purity (5).Toxicity and Safety in Scientific Experiments The safety of DIFP has been evaluated in various scientific experiments. DIFP has been tested for acute oral toxicity in rats and was found to be non-toxic up to a dose of 5000 mg/kg, indicating it has low toxicity (6). However, further research is necessary to evaluate the potential chronic toxicity of DIFP.Applications in Scientific Experiments DIFP has been utilized as a chiral auxiliary in the synthesis of complex molecules, such as natural products and pharmaceuticals. It has also been used to prepare mono- and disaccharides, as well as glycosides and glycoconjugates (7). DIFP can be utilized for the selective protection of the hydroxyl groups in monosaccharides, as well as for the preparation of ?-fructofuranosyl and ?-glucopyranosyl donors (8).Current State of Research Recent research has focused on the synthesis and characterization of DIFP, as well as the evaluation of its biological properties. Researchers are investigating the potential of DIFP as a chiral auxiliary in various synthetic procedures, as well as the development of new sugar mimetics with enhanced biological activities (9).Potential Implications in Various Fields of Research and Industry The potential implications of DIFP in various fields of research and industry include the development of new pharmaceuticals and therapeutic agents, as well as the production of novel materials and biomolecules. Its applications in synthetic organic chemistry and biochemistry are vast and varied (10).Limitations and Future Directions Despite its numerous applications, certain limitations and future directions must be considered. For instance, DIFP may have potential toxicological effects that require further investigation. Additionally, future research should aim to find new, innovative methods for the synthesis and utilization of DIFP.Future Directions Numerous future directions for research on DIFP exist. For instance, further research is necessary to evaluate the potential toxicological effects of DIFP. Additionally, new synthetic methods for the preparation of DIFP derivatives, as well as its applications in industrial processes, need to be investigated. Finally, the development of new sugar mimetics and glycosylating reagents that utilize DIFP as a starting material is an exciting direction for potential future research.Conclusion DIFP is a cyclic acetal derivative of fructose that has found significant applications in various scientific fields, including organic chemistry, biochemistry, and pharmacology. It exhibits numerous biological properties and has been shown to be an excellent reagent for various synthetic and analytical procedures. The current state of research on DIFP is focused on its synthesis and characterization, as well as the evaluation of its biological properties. Its potential implications in various fields of research and industry make it an exciting area for future research.CAS Number20880-92-6Product Name2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranoseIUPAC Name[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methanolMolecular FormulaC??H??O?Molecular Weight260.28 g/molInChIInChI=1S/C12H20O6/c1-10(2)15-7-5-14-12(6-13)9(8(7)16-10)17-11(3,4)18-12/h7-9,13H,5-6H2,1-4H3/t7-,8-,9+,12+/m1/s1InChI KeyPSSHGMIAIUYOJF-XBWDGYHZSA-NSMILESCC1(OC2COC3(C(C2O1)OC(O3)(C)C)CO)CSynonyms2,3:4,5-Bis-O-(1-methylethylidene)-?-D-fructopyranose; USP Topiramate Related Compound ACanonical SMILESCC1(OC2COC3(C(C2O1)OC(O3)(C)C)CO)CIsomeric SMILESCC1(O[C@@H]2CO[C@@]3([C@H]([C@@H]2O1)OC(O3)(C)C)CO)C CAS No: 20880-92-6 Synonyms: Diacetone-D-fructose2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranoseDiacetonefructose?MDL No: MFCD00022183 Chemical Formula: C12H20O6 Molecular Weight: 260.28References: 1. Popek T, Lis T, Carbohydr. Res. 2002, 30, p7872. Maryanoff BE, Nortey SO, Gardocki JF, Shank RP, et al., J. Med. Chem. 1987, 30, p880