16975-88-5

Upstream product

• 67-56-1 methanol 
• 57-48-7 D-Fructose 
• 57-48-7 fructose 
• 57-50-1 Sucrose 
• 6347-01-9 fructopyranose 
• 470-23-5 D-fructose 
• 7660-25-5 D-fructose 
• 7647-01-0 hydrogenchloride 
• 25018-67-1 1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 
• 76880-54-1 benzyl α-D-fructofuranoside 
• 148979-53-7 D-fructose diethyl dithioacetal 
• 2280-44-6 D-Glucose 
• 530-26-7 D-Mannose 
• 50-99-7 D-glucose 

Downstream Products

• 23259-20-3 1.3.4.6-Tetramethyl-β-D-methylfructosid 
• 57-48-7 fructose 
• 76880-54-1 benzyl α-D-fructofuranoside 
• 128804-06-8 methyl 1,6-bis-O-(triphenylmethyl)-α-D-fructofuranoside 
• 429675-58-1 (R)-1-((2S,3S,4R,5R)-2-Allyl-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-prop-2-en-1-ol 
• 429675-56-9 (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-iodomethyl-1,7-dioxa-spiro[4.4]nonane 
• 429675-61-6 (2R,3R,3aS,5R,6R,6aS)-3a-Allyl-6-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]furan-3-ol 
• 429675-57-0 (2R,3S,4R,5R)-2-Allyl-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde 
• 111085-79-1 1-(1,3,4,6-tetra-O-benzyl-α-D-fructofuranosyl)-2-propene 
• 111085-83-7 1-(3,4,6-tri-O-benzyl-α-D-fructofuranosyl)-2-propene 
• 53263-31-3 methyl O³,O⁴-phenylboranediyl-β-D-psicofuranoside 
• 10225-44-2 benzyl-(tetra-O-acetyl-α-D-fructofuranoside) 
• 147694-28-8 4-Bromo-benzoic acid (2R,3R,4S,5S)-2,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-5-methoxy-4-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-tetrahydro-furan-3-yl ester 

Relevant academic research and scientific papers

Tin Grafted on Modified Alumina-Catalyzed Isomerisation of Glucose to Fructose

The present study focuses on designing a catalyst based on hot water treated alumina (Al2O3-HWT) for the conversion of glucose to fructose. The glucose isomerisation reactions are performed with tin incorporated on parent Al2O3 and Al2O3-HWT in methanol. 0.5 wt% Sn/Al2O3-HWT affords a combined yield of fructose and methylfructoside (30.4%) which is two-fold higher than that obtained with 0.5wt% Sn/Al2O3 (15.1%), implying the importance of hot water treatment of Al2O3. Al2O3-HWT shows a very broad peak centred around 3440 cm-1, which could be assigned to OH stretching band of gibbsite, γ-Al(OH)3 which significantly diminished after solid state ion-exchange with SnCl4.5H2O (0.5 wt% Sn/Al2O3-HWT). UV-Vis diffused reflectance spectrum of 0.5 wt% Sn/Al2O3-HWT displays a peak centered at 241 nm, which can be ascribed to the incorporation of tin into the alumina network. XRD patterns of 0.5, 3 and 5 wt% Sn/Al2O3-HWT show that no peak corresponding to SnO2 is formed. Importantly, 0.5wt% SnO2/Al2O3-HWT exhibits a low activity, giving 13.2% of the total yield of fructose and methylfructoside, respectively, compared to 0.5wt% Sn/Al2O3-HWT (30.4% fructose), signifying the role of incorporated tin into the alumina network.

Synthesis of natural/13C-enriched D-tagatose from natural/13C-enriched D-fructose

A concise, easily scalable synthesis of a rare ketohexose, D-tagatose, was developed, that is compatible with the preparation of D-[UL-13C6]tagatose. Epimerization of the widely available and inexpensive ketohexose D-fructose at the C-4 position via an oxidation/reduction (Dess-Martin periodinane/NaBH4) was a key step in the synthesis. Overall, fully protected natural D-tagatose (3.21 g) was prepared from D-fructose (9 g) on a 50 mmol scale in 23% overall yield, after five steps and two chromatographic purifications. D-[UL-13C6]Tagatose (92 mg) was prepared from D-[UL-13C6]fructose (465 mg, 2.5 mmol) in 16% overall yield after six steps and four chromatographic purifications.

DITHIOLSACCHARIDE MUCOLYTIC AGENTS AND USES THEREOF

There are provided, inter alia, methods for decreasing mucus elasticity or decreasing mucus viscosity in a subject in need thereof, the methods including administering to the subject an effective amount of a dithiolsaccharide mucolytic agent, and compounds and pharmaceutical compositions useful for the methods.

A Systematic Study of Metal Triflates in Catalytic Transformations of Glucose in Water and Methanol: Identifying the Interplay of Br?nsted and Lewis Acidity

The specific type of acidity associated with the given metal trifloromethanesulfonates (Br?nsted or Lewis acidity) dramatically influences the course of reactions, and it is possible to select for disaccharides, fructose, methyl glucosides, or methyl levulinate. Glucose is transformed into a range of value-added molecules in water and methanol under the action of acidic metal triflates as catalysts, including their analogous Br?nsted acid-assisted or Br?nsted base-modified systems. A systematic study is presented of a range of metal triflates in methanol and water, pinning down the preferred conditions to select for each product.

Kinetic analysis of hexose conversion to methyl lactate by Sn-Beta: Effects of substrate masking and of water

Simple sugars show promise as substrates for the formation of fuels and chemicals using heterogeneous catalysts in alcoholic solvents. Sn-Beta is a particularly well-suited catalyst for the cleavage, isomerization and dehydration of sugars into more valuable chemicals. In order to understand these processes and save resources and time by optimising them, kinetic and mechanistic analyses are helpful. Herein, we study substrate entry into the Sn-Beta-catalysed methyl lactate process using abundant hexose substrates. NMR spectroscopy is applied to show that the formation of methyl lactate occurs in two kinetic regimes for fructose, glucose and sucrose. The majority of methyl lactate is not formed from the substrate directly, but from methyl fructosides in a slow regime. At 160 °C, more than 40% of substrate carbon are masked (i.e. reversibly protected in situ) as methyl fructosides within a few minutes when using hydrothermally synthesised Sn-Beta, while more than 60% methyl fructosides can be produced within a few minutes using post-synthetically treated Sn-Beta. A significant fraction of the substrate is thus masked by rapid methyl fructoside formation prior to subsequent slow release of fructose. This release is the rate-limiting step in the Sn-Beta-catalysed methyl lactate process, but it can be accelerated by the addition of small amounts of water at the expense of the maximum methyl lactate yield.

ISOMERISATION OF C4-C6 ALDOSES WITH ZEOLITES

The present invention relates to isomerization of C4-C6 aldoses to their corresponding C4-C6 ketoses. In particular, the invention concerns isomerization of C4-C6 aldoses over solid zeolite catalysts free of any metals other than aluminum, in the presence of suitable solvent(s) at suitable elevated temperatures. C6 and C5 aldose sugars such as glucose and xylose, which are available in large amounts from biomass precursors, are isomerized to fructose and xylulose respectively, in a one or two-step process over inexpensive commercially available zeolite catalysts, containing aluminum as the only metal in the catalyst. The ketoses obtained are used as sweeteners in the food and/or brewery industry, or treated to obtain downstream platform chemicals such as lactic acid, HMF, levulinic acid, furfural, MMHB, and the like. FIG. 7

METHOD OF PREPARING FURFURAL COMPOUNDS

Provided is a two-step method of producing a compound of chemical formula 1 in the presence of an alcohol solvent and a Group 3B metal catalyst or a salt thereof, comprising a first step comprising alkylation or isomerization of an aldohexose-containing substrate to obtain an intermediate, and a second step comprising dehydration of the intermediate to produce a compound of chemical formula 1. Preferably, additional solvent and/or catalyst are not added in the second step.

Efficient isomerization of glucose to fructose over zeolites in consecutive reactions in alcohol and aqueous media

Isomerization reactions of glucose were catalyzed by different types of commercial zeolites in methanol and water in two reaction steps. The most active catalyst was zeolite Y, which was found to be more active than the zeolites beta, ZSM-5, and mordenite. The novel reaction pathway involves glucose isomerization to fructose and subsequent reaction with methanol to form methyl fructoside (step 1), followed by hydrolysis to re-form fructose after water addition (step 2). NMR analysis with 13C-labeled sugars confirmed this reaction pathway. Conversion of glucose for 1 h at 120 C with H-USY (Si/Al = 6) gave a remarkable 55% yield of fructose after the second reaction step. A main advantage of applying alcohol media and a catalyst that combines Bronsted and Lewis acid sites is that glucose is isomerized to fructose at low temperatures, while direct conversion to industrially important chemicals like alkyl levulinates is viable at higher temperatures.

An efficient procedure for synthesis of fructose derivatives

We developed a very simple procedure to prepare fructose derivatives or fructosides. This procedure waived the requirement of isomer separation, which is usually a very common and difficult problem in fructose derivative syntheses. In this procedure, the hydroxyl groups were differentiated to expedite the preparation of many kinds of other fructose derivatives and the alkoxy group in the fructosides could exchange easily with alcohols under the mild acidic condition, which offered a new method to synthesize other fructosides through alcohol exchanging. By using this procedure, we successfully synthesized fluorogenic fructose derivatives for high throughput enzyme screening. This methodology could expand the usage of the abundant fructose in organic synthesis.

Conversion of fructose into 5-hydroxymethylfurfural (HMF) and its derivatives promoted by inorganic salt in alcohol

The conversion of d-fructose to 5-hydroxymethylfurfural (HMF) on a 1 mmol scale was achieved in good yield (68%) using NH4Cl as catalyst in isopropanol at 120 °C. About 3% of 5-i-propoxymethylfurfural was formed. The reaction in ethanol at 100 °C on a 10 g scale gave a total yield of HMF and 5-ethoxymethylfurfural of 42%. No mineral acid such as H2SO 4 and HCl are required.