1589590-87-3

Usage

Uses

Used in Pharmaceutical Industry:
Canagliflozin α Isomer is used as an active pharmaceutical ingredient for the development of medications targeting type 2 diabetes and obesity. Its role as an SGLT2 inhibitor helps regulate glucose levels in the body, providing a potential therapeutic option for patients suffering from these conditions.
Used in Research and Development:
Canagliflozin α Isomer serves as a valuable compound in the research and development of new drugs and therapies. Its unique properties allow scientists to study its interactions with biological systems and explore its potential in treating various diseases beyond diabetes and obesity.
Used in Quality Control and Impurity Profiling:
In the pharmaceutical manufacturing process, Canagliflozin α Isomer can be used as a reference material for quality control and impurity profiling. This helps ensure the safety, efficacy, and purity of the final drug product by comparing it to the known properties of the α Isomer.
Used in Drug Interaction Studies:
Canagliflozin α Isomer can be employed in drug interaction studies to understand its potential effects when combined with other medications. This information is crucial for healthcare providers and patients to make informed decisions about drug combinations and potential side effects.

Upstream product

• 1132832-76-8 1-[1-hydroxy-2,3,4,6-tetra-O-(trimethylsilyl)-β-D-glucopyranosyl]-4-methyl-3-[[5-(4-fluorophenyl)-2-thienyl]methyl]benzene 
• 866607-35-4 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1030825-21-8 methyl 1-C-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methyl-phenyl)-D-glucopyranoside 
• 1432591-75-7 1,6-anhydro-2,4-di-O-tert-butyldiphenylsilyl-β-D-glucopyranose 
• 498-07-7 levoglucosan 
• 1432591-84-8 2,4-di-O-tert-butyldiphenylsilyl-1-C-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-β-D-glucopyranoside 
• 32741-93-8 1,6-anhydro-β-D-glucopyranose 2,4-O-phenylboronate 
• 1030825-20-7 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide 
• 898566-17-1 (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) 
• 1358581-37-9 (2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 1335-57-5 3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 1213234-53-7 1,2,3,4,6-penta-O-pivaloyl-D-glucopyranoside 

Downstream Products

• 1951467-29-0 [2-methyl-5-(β-D-glucopyranosyl)phenyl][5-(4-fluorophenyl)-2-thienyl]methanol 
• 928672-86-0 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene hydrate 
• 1432187-87-5 canagliflozin L-phenylalanine complex 
• 1432187-89-7 canagliflozin D-proline complex 
• 1409936-69-1 (2S,3R,4R,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol citric acid co-crystal 

Relevant academic research and scientific papers

Stereoselective Preparation of C-Aryl Glycosides via Visible-Light-Induced Nickel-Catalyzed Reductive Cross-Coupling of Glycosyl Chlorides and Aryl Bromides

A nickel-catalyzed cross-coupling reaction of glycosyl chlorides with aryl bromides has been developed. The reaction proceeds smoothly under visible-light irradiation and features the use of bench-stable glycosyl chlorides, allowing the highly stereoselective synthesis of C-aryl glycosides. (Figure presented.).

METHOD FOR PRODUCING C-ARYL GLYCOSIDE DERIVATIVE

PROBLEM TO BE SOLVED: To provide a method that can produce a C-aryl glycoside derivative stably and inexpensively. SOLUTION: A method for producing a C-aryl glycoside derivative includes the step of mixing, for example, in an organic solvent, the following benzyl-protected C-aryl glycoside derivative (IaA), at least one silyl compound selected from trimethylsilyl chloride and trimethylsilyl bromide, and an alkali metal iodide, thereby producing the following C-aryl glycoside derivative (IIaA). SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Preparation method of SGLT-2 inhibitor and intermediate

The invention discloses a preparation method of an SGLT-2 inhibitor and an intermediate. The method comprises the following steps: (1) reacting a compound A with chlorosilane under the action of an acid-binding agent to generate a compound B; (2) mixing the compound B and a compound C to obtain a compound D; and (3) reacting the compound D with a reducing agent and a catalyst to obtain the SGLT-2 inhibitor compound.

Preparation method and application of canagliflozin alpha isomer

The invention discloses a preparation method and application of a canagliflozin alpha isomer, the preparation method comprises the following steps: in the presence of Lewis acid, a compound of formulaIV and a reducing agent are subjected to a reduction reaction in an organic solvent to obtain the canagliflozin alpha isomer, wherein the lewis acid is a mixture of trifluoroacetic acid and trimethylsilyl trifluoromethanesulfonate; the reducing agent is 1, 1, 3, 3-tetramethyldisiloxane. The preparation method is simple, the high-purity canagliflozin related substance reference substance can be rapidly obtained, the yield of the product canagliflozin alpha isomer is 37.5%, the purity is as high as 97.61%, the purity requirement of a standard substance is completely met, and the canagliflozin alpha isomer can be used as the standard substance and can be applied to quality control and research of canagliflozin bulk drugs. Therefore, the quality control level of canagliflozin is improved, andthe clinical medicinal safety is ensured.

Preparation method of canagliflozin

The invention discloses a preparation method of canagliflozin. According to the method, the reaction of each step in a route is improved, so that the conversion rate of raw materials is increased, andintroduction of potential toxic compounds is avoided. In addition, reaction conditions are mild; operation is simple; purity of an obtained product is high; quality of drugs is improved; and the preparation method is suitable for industrial production.

Syntheses of SGLT2 inhibitors by Ni- And Pd-catalyzed fukuyama coupling reactions

Nickel- and palladium-catalyzed Fukuyama coupling reactions of a D-gluconolactone-derived thioester with arylzinc reagents at ambient temperature provided the corresponding multifunctional aryl ketones in high yield. Ligand screening for the nickel-catalyzed Fukuyama coupling reactions indicated that 1,2- bis(dicyclohexylphosphino)ethane (dCype) served as a superior supporting ligand to improve the product yield. In addition, Pd/C was a practical alternative that enabled ligand-free Fukuyama coupling reactions and was efficiently applied to the key C-C bond-forming step to prepare canagliflozin and dapagliflozin, which are diabetic SGLT2 inhibitors of current interest.

Preparation method of canagliflozin

The invention relates to a synthesis method of canagliflozin. According to the synthesis method, 4-fluorophenylboronic acid is taken as an initial raw material to be coupled with 5-bromo-thiophene-2-formaldehyde to synthesize 5-(4-fluorophenyl)thiophene-2-formaldehyde, the 5-(4-fluorophenyl)thiophene-2-formaldehyde undergoes reduction and chlorination and then undergoes Friedel-Crafts alkylation reaction with 4-bromotoluene to synthesize 2-(2-methyl-5-bromobenzyl)-5-(4-fluorophenyl)thiophene, and the 2-(2-methyl-5-bromobenzyl)-5-(4-fluorophenyl)thiophene undergoes condensation, etherificationand methoxyl removal with 2,3,4,6-tetra-O-trimethylsilyl-D-gluconolactone to obtain the hypoglycemic drug canagliflozin. The preparation method has the following advantages: compared with the conventional preparation methods, the synthesis process takes the 4-fluorobenzeneboronic acid as an initial raw material, so that the raw material is cheap and easy to get, the process is easy to realize industrialization, the synthesis route is short and the operation is easy; in the synthesis process, bromine is not used or butyl lithium does not need to be used twice, so that the risk of the process can be reduced; in addition, the preparation method is capable of improving the yield of canagliflozin products to 70% or more.

Preparation method of canagliflozin

The invention relates to a preparation method of canagliflozin, and the preparation method is characterized in that the preparation method comprises the following steps: 1) reacting 2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl) methyl ] thiophene with an alkaline reagent and 2,3,4, 6-tetra-O-(trimethylsilyl)- D- glucolactone under a low-temperature condition, and carrying out methylation and deprotection reaction with a methanol solution of methanesulfonic acid to generate an intermediate 1; 2) under a low-temperature condition, reacting the intermediate 1 with triethyl silane and boron trifluoride diethyl etherate, and carrying out post-treatment to obtain an intermediate 2; 3) under a low-temperature condition, reacting the intermediate 2 with an organic base, DMAP and acetic anhydride,and purifying to obtain an intermediate 3; and 4) reacting the intermediate 3 with an alkaline water solution, and purifying after the reaction to obtain the canagliflozin. The method is mild in conditions, safe to operate, simple in post-treatment and high in product purity, no alpha-isomer is detected; the product is safer.

Preparation method of canagliflozin

The invention belongs to the technical field of chemical synthesis of medicines, and concretely relates to a preparation method of canagliflozin. The preparation method comprises the following steps:carrying out an acetylation and bromination reaction on d-glucose used as a starting raw material in order to prepare bromotetraacetylglucose; carrying out a Grignard exchange reaction on 2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene and a Grignard reagent at a low temperature, and reacting the obtained reaction product with the bromotetraacetylglucose to form an acetyl protected intermediate; and reacting the intermediate with an alkaline solution, and purifying the obtained reaction product to obtain the canagliflozin. The preparation method has the advantages of mild conditions, safety in operation and simple post-treatment; and the product has a high purity, a detection result shows that the product contains no alpha-isomer, and the product is safe.

Carbon-aryl glycoside SGLT-2 inhibitor precursor and synthesis method thereof

The invention relates to a plurality of carbon-aryl glycoside SGLT-2 inhibitor precursors and a synthesis method thereof. The method takes glycosyl bromide and aryl iodide (bromide) as substrates, thesubstrates react for 1-2 days through ice water bath and the room temperature mixing condition under the effects of a catalyst, a ligand, a reducing agent and an additive, and a precursor compound ofcarbon-aryl glycoside SGLT-2 inhibitor drug is obtained. The synthesis method has the advantages that the precursor compound is convenient to hydrolyze, the conversion rate is high, the catalyst metal is cheap, the product is easily and massively prepared and not prone to deteriorating, the reaction is moderate, one-pot reaction and one-step reaction are achieved, the steps are simple, the methodis safe to operate, the yield is high, and the stereoscopic selectivity is good.