461432-25-7

Usage

Uses

Used in Pharmaceutical Industry:
D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-, tetraacetate, (1S)is used as a pharmaceutical compound for the treatment of type 2 diabetes. It functions as an SGLT2 inhibitor, which helps to reduce glucose absorption in the body by inhibiting the sodium-glucose transporter 2 in the kidneys. This action leads to a decrease in blood glucose levels, providing a beneficial effect for patients with type 2 diabetes.
Used in Drug Development:
In the field of drug development, Dapagliflozin Tetraacetate serves as a valuable compound for the research and development of new medications targeting type 2 diabetes and related metabolic disorders. Its unique chemical structure and SGLT2 inhibitory properties make it a promising candidate for the design and synthesis of novel therapeutic agents.
Used in Research Applications:
Dapagliflozin Tetraacetate is also utilized in research settings to study the mechanisms of glucose absorption and regulation in the body. It can be employed as a tool compound to investigate the role of SGLT2 in glucose homeostasis and to explore potential targets for the development of new treatments for diabetes and other related conditions.

Upstream product

• 604-69-3 β-D-glucose pentaacetate 
• 1103738-29-9 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 461432-26-8 dapagliflozin 
• 75-36-5 acetyl chloride 
• 1318794-57-8 4-bromo-1-chloro-2-[(4-ethoxyphenyl)(methoxy)methyl]benzene 
• 1103738-26-6 (2-chloro-5-iodo-phenyl)-(4-ethoxyphenyl)methanone 
• 1280647-32-6 (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanol 
• 1298086-15-3 2-((benzyloxy)(4-ethoxyphenyl)methyl)-4-bromo-1-chlorobenzene 
• 461432-23-5 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene 
• 461432-22-4 (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone 
• 21900-52-7 5-bromo-2-chloro-benzoyl chloride 
• 21739-92-4 5-bromo-2-chlorobenzoic acid 

Downstream Products

• 461432-26-8 dapagliflozin 
• 1318793-71-3 1-{4-chloro-3-[(dimethyl)(4-ethyloxyphenyl)methyl]phenyl}-1-deoxy-β-D-glucopyranose 
• 915095-99-7 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-trityl triacetate 
• 1417573-74-0 1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-D-glucopyranoside 
• 1204222-85-4 (2S,3R,4R,5S,6R)-2-(4-chloro-3-((4-ethoxyphenyl)(hydroxy)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1018899-04-1 (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxybenzyl)phenyl]-6-(methylsulfanyl)tetrahydro-2-H-pyran-3,4,5-triol 
• 864070-44-0 empagliflozin 

Relevant academic research and scientific papers

Copper-Catalyzed Arylation of Benzylic C-H bonds with Alkylarenes as the Limiting Reagents

A novel copper-catalyzed arylation of benzylic C-H bonds with nucleophilic arylboronic acids has been developed that provides an efficient way to synthesize various 1,1-diarylalkanes with a broad substrate scope and excellent functional group compatibilit

PREPARATION OF HIGHLY PURE AMORPHOUS DAPAGLIFLOZIN

A novel and improved process for the preparation of amorphous dapagliflozin is disclosed. The present invention further provides pharmaceutical compositions containing amorphous dapagliflozin, optionally in a combination with one or more other active substances and methods for making the same.

Novel preparation process of C-glucoside derivative

The invention relates to a preparation method of a compound as shown in a formula (VIII), which specifically comprises the following steps: reacting a compound as shown in a formula I with an acylation reagent under the action of an alkaline condition and a catalyst to obtain a compound as shown in a formula II; reacting the compound shown in the formula II with boron trihalide to obtain a compound shown in a formula III; under an alkaline condition, removing a protecting group from the compound shown in the formula III to obtain a compound shown in a formula IV; catalyzing the compound as shown in the formula IV and the compound as shown in the formula V by a phase transfer catalyst under an alkaline condition to obtain a compound as shown in a formula VI; reacting the compound shown in the formula VI with an acylation reagent under an alkaline condition under the action of a catalyst to obtain a compound shown in a formula VII; and under an alkaline condition, removing a protecting group from the compound shown in the formula VII to obtain a compound shown in a formula VIII.

Preparation method of dapagliflozin

The invention relates to a preparation method of dapagliflozin. The preparation method comprises the following steps: by using 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene as an initial raw material, reacting with magnesium by using iodine granules as an initiator to prepare a Grignard reagent of iodo-benzene; carrying out bromination reaction on peracetylated sugar and hydrogen bromide in an aceticacid solution to prepare 2,3,4,6-tetraacetylglucosamine bromide; adding the prepared Grignard reagent of iodo-benzene into a methylbenzene/tetrahydrofuran solution, dropwise adding a rare earth catalyst and 2,3,4,6-tetraacetylglucosamine bromide into the methylbenzene/tetrahydrofuran solution, reacting to obtain an intermediate compound of dapagliflozin; and adding the prepared intermediate compound of dapagliflozin into a tetrahydrofuran/ethanol/water solution of sodium hydroxide, removing acetyl after alkaline hydrolysis, and re-crystallizing to obtain dapagliflozin. The reaction raw materials are easy to obtain, the preparation method is simple, the conditions are mild, the preparation method is safer and more environmentally friendly, the yield is high, the purity can reach 99%, and the method is suitable for large-scale production.

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.

The antidiabetic drug reaches geleg net intermediate preparation method

The invention discloses a preparation method of antidiabetic dapagliflozin intermediate, hydroxyl protected ALPHA-D-bromo-glucopyranose as shown in formula II is used as a starting material for reacting with a Grignard reagent as shown in formula III, and the reaction is carried out in the presence of a cobalt catalyst and a ligand to prepare a dapagliflozin senior intermediate as shown in formula I. The raw material and reagents required in the preparation method are relatively cheap in price, and the preparation method has the advantages of simple operation, low cost, safe and convenient operation, good yield, less environmental pollution, and very good economic effect and is suitable for industrial production.

Design, synthesis and biological evaluation of nitric oxide releasing derivatives of dapagliflozin as potential anti-diabetic and anti-thrombotic agents

The cardiovascular complications were highly prevalent in type 2 diabetes mellitus (T2DM), even at the early stage of T2DM or the state of intensive glycemic control. Therefore, there is an urgent need for the intervention of cardiovascular complications in T2DM. Herein, the new hybrids of NO donor and SGLT2 inhibitor were design to achieve dual effects of anti-hyperglycemic and anti-thrombosis. As expected, the preferred hybrid 2 exhibited moderate SGLT2 inhibitory effects and anti-platelet aggregation activities, and its anti-platelet effect mediated by NO was also confirmed in the presence of NO scavenger. Moreover, compound 2 revealed significantly hypoglycemic effects and excretion of urinary glucose during an oral glucose tolerance test in mice. Potent and multifunctional hybrid, such as compound 2, is expected as a potential candidate for the intervention of cardiovascular complications in T2DM.

PROCESS FOR THE PREPARATION OF (1S)-1,5-ANHYDRO-1-C-{4-CHLORO-3-4[(4-ETHOXYPHENYL)METHYL]PHENYL]-GLUCITOL AND ITS SOLVATE THEREOF

The present invention relates to a process for the preparation of (1S)-1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol which is represented by the following structural formula-1 and its glycerol solvate.

PROCESS FOR THE PREPARATION OF DAPAGLIFLOZIN AND ITS SOLVATE THEREOF

The present invention provides for crystalline Dapagliflozin butane –1,2– diol solvate (VIII), crystalline Dapagliflozin (S) butane –1,2– diol solvate (VIIIa) and Dapagliflozin (R) butane –1,2– diol solvate (VIIIb). The present invention also provides industrial methods for production of crystalline Dapagliflozin butane –1,2– diol solvate (VIII), crystalline 5 Dapagliflozin (S) butane –1,2– diol solvate (VIIIa) and Dapagliflozin (R) butane –1,2– diol solvate (VIIIb). The present invention further provides an industrial method production of amorphous Dapagliflozin.

Preparation methods of SGLT-2 diabetes inhibitors and intermediates thereof

The invention provides a preparation method of an intermediate compound 7 of an SGLT-2 diabetes inhibitor dapagliflozin and an intermediate compound 8 of a SGLT-2 diabetes inhibitor empagliflozin, and new synthesis method of two final products. The preparation method comprises the following steps: carrying out carbonyl group reduction and hydroxyl group protection on a (5-halo-2-chlorophenyl)(4-ethoxyphenyl)ketone compound 1 used as an initial raw material to obtain a Grignard addition reaction key compound 4, and carrying out Grignard addition and acetylation to obtain the compound 7 and the compound 8. The dapagliflozin and the empagliflozin are respectively prepared from the compound 8. The methods have the advantages of simplicity in operation, high yield, high purity of the obtained products, and suitableness for amplified production.