1079083-63-8

Basic information

• Product Name: (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• Synonyms: (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS NO: 1079083-63-8
• Molecular Weight: 548.974
• Mol File: 1079083-63-8.mol
• Article Data: 17

Chemical Properties

• Melting Point: 149-151°C
• CAS DataBase Reference: (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(1079083-63-8)
• EPA Substance Registry System: (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(1079083-63-8)

Safety Data

• Hazardous Substances Data: 1079083-63-8(Hazardous Substances Data)

Usage

Description

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate is a complex organic compound with a unique molecular structure. It is characterized by its stereochemistry, with five chiral centers resulting in a specific arrangement of atoms in three-dimensional space. (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate is derived from tetrahydro-2H-pyran and features a variety of functional groups, including acetoxymethyl, chloro, hydroxybenzyl, and triacetate moieties. Its structural complexity and functional group diversity suggest potential applications in various fields, such as pharmaceuticals, materials science, and chemical research.

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

• 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 
• 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 
• 333361-51-6 4-bromo-1-chloro-2-(4-methoxybenzyl)benzene 
• 333361-49-2 (5-bromo-2-chlorophenyl)(4-methoxyphenyl)methanone 
• 333359-90-3 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-methoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1118566-45-2 (1S)-1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol 
• 461432-24-6 (3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 461432-22-4 (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone 
• 21900-52-7 5-bromo-2-chloro-benzoyl chloride 

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 articles and documents

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, 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.

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.