915095-99-7

Usage

Uses

Used in Pharmaceutical Industry:
(1S)-1,5-anhydro-2,3,4,6-tetra-O-acteyl-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydrofu-ran-3-yl]oxy]phenyl] methyl]phenyl]-D-Glucitol is used as a pharmaceutical intermediate for the synthesis of Empagliflozin, a medication used to treat type 2 diabetes. It serves as an Empagliflozin intermediate, playing a crucial role in the development and production of this therapeutic agent.
Used in Chemical Production Processes:
In the chemical industry, (1S)-1,5-anhydro-2,3,4,6-tetra-O-acteyl-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydrofu-ran-3-yl]oxy]phenyl] methyl]phenyl]-D-Glucitol is utilized as a key intermediate in the synthesis of glucopyranosyl-substituted benzonitriles. These compounds are valuable for the preparation of therapeutic agents that target metabolic disorders, offering potential treatments for various conditions related to metabolic dysfunction.
Used in Laboratory Research and Development:
(1S)-1,5-anhydro-2,3,4,6-tetra-O-acteyl-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydrofu-ran-3-yl]oxy]phenyl] methyl]phenyl]-D-Glucitol is also employed in laboratory research and development processes. Its unique chemical structure and properties make it an interesting candidate for further investigation and potential applications in various fields, such as drug discovery, material science, and chemical synthesis.

Upstream product

• 915095-94-2 (3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 915095-87-3 (S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone 
• 1279691-36-9 (2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 2069942-68-1 (2S,3R,4S,5R,6R)-6-(acetoxymethyl)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 19094-56-5 2-chloro-5-iodobenzoic acid 
• 108-24-7 acetic anhydride 
• 281652-58-2 2-chloro-5-iodobenzoylchloride 
• 915095-86-2 (2-chloro-5-iodophenyl)(4-fluorophenyl)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 
• 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 
• 21739-92-4 5-bromo-2-chlorobenzoic acid 
• 333361-49-2 (5-bromo-2-chlorophenyl)(4-methoxyphenyl)methanone 
• 21900-52-7 5-bromo-2-chloro-benzoyl chloride 

Relevant academic research and scientific papers

Synthetic method of empagliflozin

The invention belongs to the technical field of raw material medicine preparation, and relates to a synthetic method of an SGLT-2 inhibitor empagliflozin, which comprises the following steps: 1) taking glucose as an initial raw material, and preparing an active intermediate 3 through full acylation, selective hydrolysis and esterification; 2) reacting the intermediate 3 with chlorobenzene under the catalysis of boron trifluoride/diethyl ether to generate an intermediate 4, and reacting the intermediate 4 with paraformaldehyde and phenoxy tetrahydrofuran to generate an intermediate 5; and 3) removing the protecting group under the action of alkali to obtain the final product empagliflozin. The method is simple to operate, low-temperature reaction in the prior art is avoided, and the purity of the obtained product is higher.

Synthetic method of empagliflozin

The invention provides a brand-new synthesis process of empagliflozin. According to the process, a boric acid ester is used for halogen removal, and specific reaction conditions are combined, so thatempagliflozin can be prepared with high yield and simplicity and convenience in operation. The synthesis method of empagliflozin has the advantages of mild reaction conditions, high total yield, few side reactions and convenience in operation, thereby being beneficial to industrial production and cost control.

Carbon-aryl glycoside SGLT-2 inhibitor precursor and synthesis method thereof

The invention relates to a plurality of carbon-aryl glycoside SGLT-2 inhibitor precursors and a synthesis method thereof. The method takes glycosyl bromide and aryl iodide (bromide) as substrates, thesubstrates react for 1-2 days through ice water bath and the room temperature mixing condition under the effects of a catalyst, a ligand, a reducing agent and an additive, and a precursor compound ofcarbon-aryl glycoside SGLT-2 inhibitor drug is obtained. The synthesis method has the advantages that the precursor compound is convenient to hydrolyze, the conversion rate is high, the catalyst metal is cheap, the product is easily and massively prepared and not prone to deteriorating, the reaction is moderate, one-pot reaction and one-step reaction are achieved, the steps are simple, the methodis safe to operate, the yield is high, and the stereoscopic selectivity is good.

Nickel-catalyzed reductive coupling of glucosyl halides with aryl/vinyl halides enabling β-selective preparation of C-aryl/vinyl glucosides

This work describes stereoselective preparation of β-C-aryl/vinyl glucosides via mild Ni-catalyzed reductive arylation and vinylation of C1-glucosyl halides with aryl and vinyl halides. A broad range of aryl halides and vinyl halides were employed to yield C-aryl/vinyl glucosides in 42%–93% yields. Good to excellent β-selectivities were obtained for C-glucosides by using tridentate ligand.

Synthesizing method suitable for industrial empagliflozin production

The invention discloses a synthesizing method suitable for industrial empagliflozin production. The synthesizing method includes: subjecting a compound as shown in formula (II) to reduction reaction to obtain a compound as shown in formula (I), and removing the protecting groups of the compound as shown in formula (I) to obtain empagliflozin. The synthesizing method has the advantages that the method is simple in process, only needs one-step reduction reaction and can effectively reduce the repeated use of high-toxicity and high-risk chemicals; in addition, the intermediate purified after derivation protection, effective process control is achieved, and product quality is increased; the method is high in practical application value and suitable for industrial production.

A PROCESS FOR THE PREPARATION OF SGLT2 INHIBITORS AND INTERMEDIATES THEREOF

The present invention relates to an industrially feasible and economically viable process for preparation of SGLT2 inhibitors of formula (X) in significantly high yield and purity.

Method for preparing empagliflozin and an intermediates thereof

The invention relates to a method for preparing empagliflozin and an intermediate thereof and the novel intermediate of the empagliflozin. The method and the novel intermediate have the advantages that reaction impurities can be controlled effectively, especially the isomer impurities are controlled outstandingly, quality control of empagliflozin active pharmaceutical ingredient production is facilitated, and convenience is brought to the researches of subsequent preparations.

A method for preparing empagliflozin

A method for preparing empagliflozin is provided. The method includes steps of preparing a composite organometallic reagent to promote condensation of (S)-4-halogen-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl) benzene and halogenated glucose, and then removing a protecting group to obtain a product, wherein the organometallic reagent is a product by mixing a Grignard reagent or a lithium chloridepromoted Grignard reagent with a lithium reagent. The organometallic reagent can allow the temperature of a coupling reaction to be increased from -78 DEG C to -10 DEG C, thus improving process reaction conditions, making operation simple and convenient, reducing byproducts and reducing the production cost. The method reduces process steps, avoids reactions at excessively low temperatures, increases the total yield and has an industrial application prospect.

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.

Industrial preparation method for empagliflozin

The invention discloses an industrial preparation method for empagliflozin. Specifically, the invention relates to a preparation method for empagliflozin as shown in formula as defined in the specification, i.e., (1S)-1,5-dehydro-1-(4-chloro-3{4-[(3S)-tetrahydrofuran-3-yloxy]benzyl}pheyl)-D-glucitol, and an intermediate prepared by using the method. The preparation method for empagliflozin in the invention is stable in process, good in reproducibility and suitable for large-scale production.