864070-37-1

Basic information

• Product Name: ((2R,3S,4R,5R,6S)-6-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)Methyl acetate
• Synonyms: ((2R,3S,4R,5R,6S)-6-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)Methyl acetate;EMpagliflozin iMpurity 5;(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;Empagliflozin impurity H;D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[(4-hydroxyphenyl)methyl]phenyl]-, (1S)-;Jardiance Impurity H;(3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS NO: 864070-37-1
• Molecular Formula: C₁₉H₂₁ClO₆
• Molecular Weight: 492.94596
• EINECS: -0
• Mol File: 864070-37-1.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 628.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.459±0.06 g/cm3(Predicted)
• PKA: 10.17±0.15(Predicted)
• CAS DataBase Reference: ((2R,3S,4R,5R,6S)-6-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)Methyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: ((2R,3S,4R,5R,6S)-6-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)Methyl acetate(864070-37-1)
• EPA Substance Registry System: ((2R,3S,4R,5R,6S)-6-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)Methyl acetate(864070-37-1)

Safety Data

• Hazardous Substances Data: 864070-37-1(Hazardous Substances Data)

Usage

Description

((2R,3S,4R,5R,6S)-6-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)Methyl acetate is a complex organic compound with a unique molecular structure. It is a derivative of the antidiabetic drug Dapagliflozin, which is a sodium-glucose transporter 2 (SGLT2) inhibitor. ((2R,3S,4R,5R,6S)-6-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)Methyl acetate exhibits a series of chiral centers, resulting in multiple stereoisomers, and features a tetrahydrofuran ring and a chlorophenyl group. Its molecular structure suggests potential applications in various fields, particularly in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
((2R,3S,4R,5R,6S)-6-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)Methyl acetate is used as a pharmaceutical intermediate for the development of new drugs targeting the treatment of diabetes. As a derivative of Dapagliflozin, it may possess similar inhibitory effects on SGLT2, potentially leading to improved glucose regulation and management of diabetes.
Used in Medicinal Chemistry Research:
((2R,3S,4R,5R,6S)-6-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)Methyl acetate can be utilized in medicinal chemistry research to explore its potential as a lead compound for the development of novel therapeutic agents. Its unique structure and functional groups may offer new avenues for the design of drugs with enhanced efficacy, selectivity, and safety profiles.
Used in Drug Synthesis:
((2R,3S,4R,5R,6S)-6-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)Methyl acetate can be employed as a key building block in the synthesis of more complex drug molecules. Its versatile structure allows for further chemical modifications and functionalization, enabling the creation of new drug candidates with improved pharmacological properties.

Upstream product

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• 32469-28-6 (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one 
• 21739-92-4 5-bromo-2-chlorobenzoic acid 
• 21900-52-7 5-bromo-2-chloro-benzoyl chloride 
• 461432-24-6 (3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 461432-23-5 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene 
• 461432-22-4 (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone 
• 1459754-32-5 4-(2-chloro-5-iodobenzyl)phenol 
• 1459754-40-5 (2-chloro-5-iodophenyl)(4-hydroxyphenyl)methanone 
• 1459754-39-2 (2-chloro-5-iodophenyl)(4-methoxyphenyl)methanone 
• 281652-58-2 2-chloro-5-iodobenzoylchloride 
• 19094-56-5 2-chloro-5-iodobenzoic acid 
• 333361-51-6 4-bromo-1-chloro-2-(4-methoxybenzyl)benzene 
• 333361-49-2 (5-bromo-2-chlorophenyl)(4-methoxyphenyl)methanone 

Downstream Products

• 912917-85-2 (2S,3S,4R,5R,6R)-2-(3-(4-acetoxybenzyl)-4-chlorophenyl)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1620758-33-9 (2S,3R,4R,5S,6R)-2-{4-chloro-3-[4-(tetrahydrofuran-3(R)-yloxy)benzyl]phenyl}-6-hydroxymethyltetrahydro-2H-pyran-3,4,5-triol 
• 864070-44-0 empagliflozin 
• 1118566-49-6 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-(2-morpholinoethoxy)ethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1118567-51-3 tert-butyl 2-(2-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenoxy)ethoxy)ethylcarbamate 
• 1118567-15-9 (2S,3R,4R,5S,6R)-2-(3-(4-(2-(2-bromoethoxy)ethoxy)benzyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1118566-88-3 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(3-cyclopropylprop-2-ynyloxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1118566-63-4 4-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenoxy)but-2-ynyl methanesulfonate 
• 1118567-23-9 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-(1-methylcyclopropoxy)ethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1118567-05-7 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1118567-09-1 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-(cyclohex-2-enyloxy)ethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1210040-71-3 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-((E)-3-cyclopropylallyloxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1118567-12-6 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-(2-fluoroethoxy)ethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1118567-14-8 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-(2,2-difluoroethoxy)ethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 

Relevant articles and documents

Synthesis of metabolites of dapagliflozin: an SGLT2 inhibitor

Abstract: Dapagliflozin is one of the gliflozin class drugs, useful for the treatment of type-2 diabetes. Dapagliflozin undergoes extensive metabolism and transforms to metabolites in humans. The contribution of pharmacologically active metabolites in drug discovery and development is significant. A streamlined synthetic approach is devised to access three metabolites of dapagliflozin namely, benzylic hydroxy dapagliflozin, oxo dapagliflozin and desethyl dapagliflozin. Two synthetic protocols have been proposed for the synthesis of benzylic hydroxy dapagliflozin and oxo dapagliflozin. An enantioselective deethylation of dapagliflozin is also reported. Graphic abstract: Synthesis of three metabolites of Dapagliflozin namely benzylic hydroxy dapagliflozin, oxo dapagliflozin and desethyl dapagliflozin is reported from commercially accessible raw materials.[Figure not available: see fulltext.]

Synthetic method for empagliflozin related substance IMPD

The invention discloses a synthetic method for empagliflozin related substance IMPD. In a current synthetic method of IMPD, a whole synthetic route is longer and the total yield is lower. The synthetic method provided by the invention comprises the following steps: performing hydroxylation by using (2-chloro-5-iodophenyl)(4-fluorophenyl)methanone as a raw material to obtain (2-chloro-5-iodophenyl)(4-hydroxyphenyl)methanone, performing a reaction by using a carbonyl reducing agent to obtain 4-(5-iodo-2-chlorobenzyl)phenol, protecting phenolic hydroxyl groups by using protecting groups such as TBDMS, performing metallization of aromatic iodide by adopting a relatively stable and safe Grignard reagent i-PrMgCl.LiCl, performing methyl glucoside reduction by using a Lewis acid catalyst, and finally performing quenching to obtain the empagliflozin related substance IMPD. The synthetic method provided by the invention has the advantages of an abundant raw material source, a simple, quick andhigh-efficiency reaction, milder reaction conditions, a higher total yield and low costs.

PROCESS FOR PREPARATION OF DAPAGLIFLOZIN AND INTERMEDIATES THEREOF

Processes for the preparation of dapagliflozin reduce or eliminate impurities in dapagliflozin, preferably individual impurities are not more than 0.15% by HPLC.