1079083-63-8

Usage

Uses

Used in Pharmaceutical Industry:
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate is used as a synthetic intermediate for the development of novel pharmaceutical compounds. Its unique structure and functional groups make it a promising candidate for the design and synthesis of new drugs with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate serves as a valuable compound for studying reaction mechanisms, exploring new synthetic routes, and understanding the relationship between molecular structure and chemical properties.
Used in Materials Science:
The compound's structural features and functional group diversity make it a candidate for use in the development of new materials with specific properties, such as improved stability, reactivity, or selectivity. It may be employed in the design of catalysts, sensors, or other advanced materials with applications in various industries.
Used in the Synthesis of Nitric Oxide Releasing Derivatives:
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate is used as a reagent in the design and synthesis of nitric oxide releasing derivatives of dapagliflozin. These derivatives have potential applications as antidiabetic and antithrombotic agents, offering new therapeutic options for patients with diabetes and related conditions.

Upstream product

• 461432-23-5 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene 
• 864070-18-8 4-(5-bromo-2-chlorobenzyl)phenol 
• 1204220-63-2 (2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 864070-37-1 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 912917-85-2 (2S,3S,4R,5R,6R)-2-(3-(4-acetoxybenzyl)-4-chlorophenyl)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1298086-15-3 2-((benzyloxy)(4-ethoxyphenyl)methyl)-4-bromo-1-chlorobenzene 
• 1280647-32-6 (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanol 
• 1103738-26-6 (2-chloro-5-iodo-phenyl)-(4-ethoxyphenyl)methanone 
• 1210040-47-3 (2S, 3R, 4S, 5S, 6R)-2-(3-(4-methoxybenzyl)-4-chlorophenyl)-tetrahydro-6-(hydroxymethyl)-2-methoxy-2H-pyran-3,4,5-triol 
• 960494-15-9 C₃₃H₅₇ClO₇Si₄ 
• 333361-51-6 4-bromo-1-chloro-2-(4-methoxybenzyl)benzene 
• 333361-49-2 (5-bromo-2-chlorophenyl)(4-methoxyphenyl)methanone 

Downstream Products

• 1291094-41-1 acetic acid (2R,3R,4R,SS,6S)-3,4,5-triacetoxy-6-[4-chloro-3-{4-hydroxy-3-nitro-benzyl}-phenyl]-tetrahydro-pyran-2-ylmethyl ester 
• 1291094-42-2 2-{4-[2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-benzyl]-2-nitro-phenoxy}-2-methyl-propionic acid ethyl ester 
• 1291094-43-3 [(2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-[(2,2-dimethyl-3-oxo-2H-1,4-benzoxazin-6-yl)methyl]phenyl]tetrahydropyran-2-yl]methyl acetate 
• 1291094-44-4 6-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one 
• 1291094-53-5 acetic acid (2R,3R,4R,SS,6S)-3,4,5-triacetoxy-6-[4-chloro-3-{3-amino-4-hydroxy-benzyl}-phenyl]-tetrahydro-pyran-2-ylmethyl ester 
• 1291094-54-6 acetic acid (2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-(2-cyano-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-tetrahydro-pyran-2-ylmethyl ester 
• 1291094-55-7 6-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-3,4-dihydro-2H-benzo[1,4]oxazine-2-carbonitrile 
• 1291094-56-8 6-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid methyl ester 
• 1291094-57-9 6-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid 
• 946525-42-4 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-cyanobenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1118566-90-7 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-acetylbenzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1204220-56-3 1-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone 
• 1416165-35-9 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(1-(ethoxyimino)ethyl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1416164-51-6 1-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone O-ethyl oxime 

Relevant academic research and scientific papers

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.

GLUCOPYRANOSE DERIVATIVES USEFUL AS SGLT2 INHIBITORS

The present invention is directed to glucopyranose derivatives of formula (I), pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.

GLUCOPYRANOSE DERIVATIVES USEFUL AS SGLT2 INHIBITORS

The present invention is directed to glucopyranose derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.

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.

Processes for the Preparation of SGLT-2 Inhibitors, Intermediates Thereof

The present invention relates to novel, improved processes for the preparation of sodium glucose co-transporter 2 (SGLT-2) inhibitors and novel intermediates thereof. More particularly, the present invention relates to a novel, improved process for the preparation of gliflozin compounds such as empagliflozin and dapagliflozin, intermediates thereof. The product obtained from the processes of present invention may be amorphous or crystalline, or in the form of amorphous/crystalline solid dispersions/solutions with pharmaceutically acceptable polymers and preparation process thereof. Also, the products obtained from the present invention may be used for the preparation of medicaments for the prevention and/or treatment of diseases and conditions associated with SGLT-2 inhibition.

A PROCESS FOR THE PREPARATION OF D-GLUCITOL, 1,5-ANHYDRO-1-C-[4-CHLORO-3-[[4- [[(3S)-TETRAHYDRO-3-FURANYL]OXY]PHENYL]METHYL]PHENYL]-, ( 1 S)

The present invention relates to a process for the preparation of D-glucitol, 1,5- anhydro-1-C-[4-chloro-3-[[ 4-[[(3S)-tetrahydro-3-furanyl)oxy )phenyl] methyl]phenyl]-, (IS) formula-1.

THE PRESENT INVENTION RELATES TO PROCESS FOR THE PREPARATION OF D-GLUCITOL, 1,5- ANHYDRO-1-C-[4-CHLORO-3-[[4-[[(3S)-TETRAHYDRO-3-FURANYL] OXY]PHENYL] METHYL]PHENYL]-, (1S) AND ITS CRYSTALLINE FORMS THEREOF.

The present invention relates to process for the preparation of D-glucitol, 1,5- anhydro-l-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl] methyl]phenyl]-, (1S) formula- 1 and its crystalline forms thereof.

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.

C- ARYL GLYCOSID DERIVATIVES, PHARMACEUTICAL COMPOSITION, PREPARATION PROCESS AND USES THEREOF

This invention relates to a kind of C-aryl glycoside derivatives, its pharmaceutical compositions, preparation methods, and uses thereof. The preparation method comprises: method 1: in a solvent, deprotecting the acetyl protecting groups of compound 1-f in the presence of a base; method 2: 1) compound 2-g reacts with via Mitsunobu reaction; 2) deprotecting the acetyl protecting groups of compound 2-f obtained from step 1; method 3: 1) compound 2-g reacts with via nucleophilic substitution reaction; 2) deprotecting the acetyl protecting groups of compound 3-f obtained from step 1. The pharmaceutical composition comprises a kind of C-aryl glycoside derivatives; it's pharmaceutically acceptable salts and/or prodrugs thereof and excipient thereof. This invention further relates to a kind of C-aryl glycoside derivatives, it's pharmaceutically acceptable salts or pharmaceutical compositions thereof for the use in preparation of a SGLT inhibitor. The C-aryl glycoside derivatives of this invention provides a new direction for the study of SGLT inhibitors.

C - aryl glucoside SGLT2 inhibitor

The invention relates to the field of medicines related to diabetes mellitus and particularly relates to a 2-type sodium-glucose co-transporter (SGLT2) inhibitor with a multi-aryl glucoside structure and shown as the specification, a preparation method thereof, a medicine composition taking the compound as an active components and an application thereof in preparing medicines for resisting diabetes mellitus.