461432-24-6

Basic information

• Product Name: (3R,4R,5R,6S)-2-(acetoxyMethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• Synonyms: (3R,4R,5R,6S)-2-(acetoxyMethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate;D-Glucopyranoside, Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-;Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucopyranoside;(3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol;EOS-61485
• CAS NO: 461432-24-6
• Molecular Formula: C₂₂H₂₇ClO₇
• Molecular Weight: 577.01932
• Mol File: 461432-24-6.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 609.6±55.0 °C(Predicted)
• Appearance: /
• Density: 1.39±0.1 g/cm3(Predicted)
• PKA: 12.59±0.70(Predicted)
• CAS DataBase Reference: (3R,4R,5R,6S)-2-(acetoxyMethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R,5R,6S)-2-(acetoxyMethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(461432-24-6)
• EPA Substance Registry System: (3R,4R,5R,6S)-2-(acetoxyMethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(461432-24-6)

Safety Data

• Hazardous Substances Data: 461432-24-6(Hazardous Substances Data)

Upstream product

• 461432-23-5 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene 
• 32469-28-6 (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one 
• 67-56-1 methanol 
• 960494-15-9 C₃₃H₅₇ClO₇Si₄ 
• 281652-58-2 2-chloro-5-iodobenzoylchloride 
• 103-73-1 Phenetole 
• 19094-56-5 2-chloro-5-iodobenzoic acid 
• 1103738-29-9 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene 
• 90-80-2 D-Glucono-1,5-lactone 
• 100227-29-0 5,6-di-O-isopropylidene-D-glucono-1,4-lactone 
• 21739-92-4 5-bromo-2-chlorobenzoic acid 
• 461432-22-4 (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone 
• 21900-52-7 5-bromo-2-chloro-benzoyl chloride 
• 75-75-2 methanesulfonic acid 

Downstream Products

• 1118566-45-2 (1S)-1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol 
• 461432-26-8 dapagliflozin 
• 1204219-27-1 (2R,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-2-d-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 461432-25-7 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 

Relevant articles and documents

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.

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.

Method for purifying dapagliflozin

The invention discloses a method for purifying dapagliflozin. The method comprises the steps of carrying out coupled reaction on 4-bromo-1-chloro-2-2-(4-ethoxybenzyl)-benzene as shon in a formula I and 2,3,4,6- tetra-O-trimethylsilyl-D-glucolactone, and removing trimethylsilyl to obtain a compound as shown in a formula II; removing methoxyl from the compound as shown in the formula II to prepare a compound as shown in a formula III; protecting hydroxyl in the compound as shown in the formula III to obtain a compound as shown in a formula IV; and finally hydrolyzing the compound as shown in the formula IV to prepare the dapagliflozin. The method is simple in process, relatively mild in operation condition and available in raw materials, and a product with higher purity can be obtained at high yield, thereby reducing the production cost.