461432-25-7

Basic information

• Product Name: D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-, tetraacetate, (1S)-
• Synonyms: D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-, 2,3,4,6-tetraacetate, (1S)-;(1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol tetraacetate;4,(1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol tetraacetate5,6,7-Tetrahydro-1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester;Dapagliflozin Intermediate 4;Dapagliflozin Intermediates;2,3,4,6-tetra-O-acetyl-1-{4-chloro-3-[(4-ethyloxyphenyl)methyl]phenyl}-1-deoxy-beta-D-glucopyranose;(2R,3S,4R,5S,6S)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate;[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]oxan-2-yl]methyl acetate
• CAS NO: 461432-25-7
• Molecular Formula: C₂₉H₃₃ClO₁₀
• Molecular Weight: 577.01932
• EINECS: 1592732-453-0
• Mol File: 461432-25-7.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 626.8±55.0 °C(Predicted)
• Appearance: /
• Density: 1.29±0.1 g/cm3(Predicted)
• Vapor Pressure: 0Pa at 25℃
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-, tetraacetate, (1S)-(CAS DataBase Reference)
• NIST Chemistry Reference: D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-, tetraacetate, (1S)-(461432-25-7)
• EPA Substance Registry System: D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-, tetraacetate, (1S)-(461432-25-7)

Safety Data

• Hazardous Substances Data: 461432-25-7(Hazardous Substances Data)

Usage

Description

D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-, tetraacetate, (1S)-, also known as Dapagliflozin Tetraacetate, is a derivative of Dapagliflozin, a sodium-glucose transporter 2 (SGLT2) inhibitor. D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-, tetraacetate, (1S)is characterized by its unique chemical structure, which includes a D-glucitol backbone with a 1,5-anhydro ring, a 4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl group, and four acetate groups. It plays a crucial role in the regulation of glucose absorption in the body.

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

• 461432-28-0 methyl-2,3,4,6-tetra-O-acetyl-1-C-(2-chloro-4'ethoxydiphenylmethan-3yl)-α-D-glucopyranose 
• 1118566-45-2 (1S)-1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol 
• 108-24-7 acetic anhydride 
• 885069-29-4 1-(5-bromo-2-chlorophenyl)-1-methylethanol 
• 1318794-41-0 1-{4-chloro-3-[(dimethyl)(4-ethyloxyphenyl)methyl]phenyl}-α/β-D-methyl glucopyranoside 
• 76008-73-6 5-Bromo-2-chloro-benzoic acid ethyl ester 
• 1318794-39-6 (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)(dimethyl)methane 
• 461432-26-8 dapagliflozin 
• 461432-23-5 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene 
• 90-80-2 D-Glucono-1,5-lactone 
• 32469-28-6 (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one 
• 461432-24-6 (3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 960494-15-9 C₃₃H₅₇ClO₇Si₄ 
• 21739-92-4 5-bromo-2-chlorobenzoic acid 

Downstream Products

• 461432-26-8 dapagliflozin 
• 1291094-21-7 acetic acid (2R,3R,4R,SS,6S)-3,4,5-triacetoxy-6-[3-(3-acetyl-4-hydroxybenzyl)-4-chloro-phenyl]-tetrahydro-pyran-2-ylmethyl ester 
• 1079083-63-8 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1291094-23-9 6-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-chromen-4-one 
• 1291094-24-0 6-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-chroman-4-one 
• 1291094-25-1 (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-hydroxy-chroman-6-ylmethyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 1291094-27-3 C₃₄H₃₇ClO₁₁ 
• 1291094-26-2 6-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-2,2-spirocyclopentyl-chroman-4-one 
• 1291094-28-4 (2S,3R,4R,5S,6R)-2-[4-chloro-3-(spiro[chromane-2,1'-cyclopentane]-6-ylmethyl)phenyl]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 
• 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 

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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.

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