Sunde-Brown, P., et al. The Journal of Organic Chemistry 87.24 (2022): 16895-16901.
Three variations of the Mitsunobu reaction were explored for the synthesis of 1-deoxymannojirimycin (1-DMJ) from D-fructose. The most efficient and scalable method yields the highest results with minimal chromatography, and can be performed on a 10 g scale. In the key step, N,O-di-Boc-hydroxylamine reacts with methyl 1,3-isopropylidene-α-D-fructofuranose under Mitsunobu conditions to form intermediate 14. Acidic hydrolysis of this intermediate produces nitrone 15, which is then quantitatively reduced via catalytic hydrogenolysis to yield 1-DMJ (4). This approach provides an overall yield of 55% from D-fructose, outperforming alternative methods (37% yield for the azide route and 29% for the nosyl route).
He, Liangtu, et al. Molecular Catalysis 508 (2021): 111584.
Dimethyl succinate (DMS), a key bio-based platform chemical, was synthesized from D-fructose under one-pot, metal-free conditions for the first time.
Typical Experiment
In a typical procedure, 75 mg of the catalyst was added to 1.5 mmol of D-fructose in 15 mL of methanol. The reaction mixture was then purged three times with oxygen, and 10 bar of O₂ was introduced. The mixture was stirred and heated to the desired temperature, which was achieved within 10-15 minutes, at which point the reaction time was set to zero. Upon completion of the reaction, stirring was stopped, and the autoclave was cooled in a water bath until the temperature dropped below 25°C. The residual pressure was released, and the autoclave was carefully opened after venting the remaining gas.
Songtawee, Siripit, et al. Biomass Conversion and Biorefinery 13.8 (2023): 6705-6714.
5-Hydroxymethylfurfural (HMF) is a key chemical intermediate used to produce a range of high-value biofuels and biochemicals. This study investigates the production of HMF through the dehydration of fructose in a biphasic system, utilizing various organic acids as catalytic promoters, including formic acid, acetic acid, lactic acid, succinic acid, and levulinic acid. Among these, acetic acid was identified as the most effective promoter for this reaction.
Fructose Dehydration to 5-HMF
The reaction was carried out in a 130-mL stainless steel autoclave equipped with a magnetic stirrer. In a typical procedure, 300 mg of D-fructose was mixed with a biphasic solvent system consisting of 9 mL of saturated NaCl aqueous solution and 21 mL of toluene (v/v ratio of 3:7). Next, 1 mL of 0.1 M organic acid (chosen from the aforementioned acids) was added to the mixture. The autoclave was then pressurized with nitrogen gas to 15 bar and heated to a set temperature between 150-200 °C. After the reaction proceeded for 30 minutes, the autoclave was cooled to ambient temperature, and the internal pressure was carefully released. The liquid product was poured into a funnel to separate the organic phase from the aqueous phase.
What is the product name of the chemical with CAS number 57-48-7?
The product name is D-Fructose.
What are some synonyms for D-Fructose?
Some synonyms for D-Fructose are fructose and D-(-)-Fructose.
What is the molecular weight of D-Fructose?
The molecular weight of D-Fructose is 180.16.
What is the molecular formula of D-Fructose?
The molecular formula of D-Fructose is C6H12O6.
What is the percentage of actives in D-Fructose?
The percentage of actives in D-Fructose is 95%.
In what physical state does D-Fructose exist?
D-Fructose exists in a solid physical state.
How is D-Fructose typically used in applications?
D-Fructose is typically used as an emulsion stabilizer and dispersing agent.
What is the CAS number of D-Fructose?
The CAS number of D-Fructose is 57-48-7.
What is the role of D-Fructose as an emulsion stabilizer?
D-Fructose helps stabilize emulsions by preventing the separation of oil and water phases.
What are the potential benefits of using D-Fructose as a dispersing agent?
Using D-Fructose as a dispersing agent can help evenly distribute particles in a solution, leading to improved product performance.
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