LX-4211

Base Information

• Chemical Name: LX-4211
• CAS No.: 1018899-04-1
• Molecular Formula: C21H25ClO5S
• Molecular Weight: 424.946
• Mol file: 1018899-04-1.mol

Synonyms:LX-4211; sotagliflozin

Chemical Property of LX-4211

Chemical Property:

• Boiling Point: 607.9±55.0 °C(Predicted)
• PKA: 12.87±0.70(Predicted)
• PSA: 104.45000
• Density: 1.37±0.1 g/cm3(Predicted)
• LogP: 3.17260

Purity/Quality:

99% ^*data from raw suppliers

Sotagliflozin(LX-4211) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Sotagliflozin is used for the treatment of patients with type 1 diabetes mellitus.
• Clinical Use: Two of the current SGLT-2 inhibitors (canagliflozin and LX-4211) have effects on SGLT-1. LX-4211 is a dual SGLT1/2 inhibitor and higher doses of canagliflozin transiently inhibit SGLT-1 in the gut due to high canagliflozin concentrations within the intestinal lumen during the period of drug absorption.

Technology Process of LX-4211

There total 54 articles about LX-4211 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.7%

[(2S,3S,4R,5S,6R)-4,5-diacetoxy-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methylthiotetrahydropyran-3-yl]acetate (1018899-03-0) → (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxybenzyl)phenyl]-6-(methylsulfanyl)tetrahydro-2-H-pyran-3,4,5-triol (1018899-04-1)

Guidance literature:

With methanol; sodium methylate; In toluene; at 113 ℃; for 0.00555556h; under 13501.4 Torr; Temperature; Pressure;

Reference yield: 97.7%

(2S,3S,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate → (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxybenzyl)phenyl]-6-(methylsulfanyl)tetrahydro-2-H-pyran-3,4,5-triol (1018899-04-1)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2.25h; Time; Inert atmosphere; Large scale;

Reference yield: 92.0%

C36H49ClO8S → (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxybenzyl)phenyl]-6-(methylsulfanyl)tetrahydro-2-H-pyran-3,4,5-triol (1018899-04-1)

Guidance literature:

With sodium methylate; In tetrahydrofuran; at 40 - 45 ℃;

upstream raw materials:

acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-2-bromo-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-tetrahydropyran-3-yl ester

sodium thiomethoxide

[(2S,3S,4R,5S,6R)-4,5-diacetoxy-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methylthiotetrahydropyran-3-yl]acetate

2-chloro-5-iodobenzoylchloride

Downstream raw materials:

[(2S,3S,4R,5S,6R)-4,5-diacetoxy-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methylthiotetrahydropyran-3-yl]acetate

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