1018899-03-0

Basic information

• Product Name: β-L-Xylopyranoside, Methyl 5-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-1-thio-, 2,3,4-triacetate,(5S)-
• Synonyms: β-L-Xylopyranoside, Methyl 5-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-1-thio-, 2,3,4-triacetate,(5S)-;(2S,3S,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(Methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate;acetic acid (2R,3S,4R,5S,6S)-4,5-diacetoxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-methylsulfanyl-tetrahydro-pyran-3 -yl ester
• CAS NO: 1018899-03-0
• Molecular Formula: C₂₇H₃₁ClO₈S
• Molecular Weight: 551.04824
• Mol File: 1018899-03-0.mol

Chemical Properties

• Boiling Point: 617.6±55.0 °C(Predicted)
• Appearance: /
• Density: 1.30±0.1 g/cm3(Predicted)
• CAS DataBase Reference: β-L-Xylopyranoside, Methyl 5-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-1-thio-, 2,3,4-triacetate,(5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: β-L-Xylopyranoside, Methyl 5-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-1-thio-, 2,3,4-triacetate,(5S)-(1018899-03-0)
• EPA Substance Registry System: β-L-Xylopyranoside, Methyl 5-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-1-thio-, 2,3,4-triacetate,(5S)-(1018899-03-0)

Safety Data

• Hazardous Substances Data: 1018899-03-0(Hazardous Substances Data)

Usage

Uses

Used in Research Applications:
β-L-Xylopyranoside, Methyl 5-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-1-thio-, 2,3,4-triacetate,(5S)is used as a research compound for studying its chemical properties and potential interactions with biological systems.
Used in Pharmaceutical Drug Development:
β-L-Xylopyranoside, Methyl 5-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-1-thio-, 2,3,4-triacetate,(5S)is used as a potential pharmaceutical agent for the development of new drugs, given its unique structural features that may offer therapeutic benefits.
Used in Laboratory Applications:
β-L-Xylopyranoside, Methyl 5-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-1-thio-, 2,3,4-triacetate,(5S)is used as a laboratory reagent for conducting experiments and testing its chemical reactions and stability under various conditions.

Upstream product

• 1018899-04-1 (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxybenzyl)phenyl]-6-(methylsulfanyl)tetrahydro-2-H-pyran-3,4,5-triol 
• 108-24-7 acetic anhydride 
• 19094-56-5 2-chloro-5-iodobenzoic acid 
• 1103738-30-2 (4-chloro-3-(4-ethoxybenzyl)phenyl)((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolan-5-yl)methanone 
• 1103738-29-9 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene 
• 1103738-26-6 (2-chloro-5-iodo-phenyl)-(4-ethoxyphenyl)methanone 
• 7647-01-0 hydrogenchloride 
• 6006-15-1 N,N-diethyl-N-isopropylamine 
• 584-08-7 potassium carbonate 
• 74-88-4 methyl iodide 
• 17314-32-8 tributyl(methylthio)stannane 

Downstream Products

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

Relevant articles and documents

Process development of sotagliflozin, a dual inhibitor of sodium- Glucose cotransporter-1/2 for the treatment of diabetes

The development of an efficient manufacturing process for sotagliflozin (LX4211), a dual inhibitor of sodium- glucose cotransporter-1/2 (SGLT-1/2) for the treatment of diabetes, is described. Sotagliflozin features five contiguous chiral centers on the carbohydrate core flanked by a thioether group and a biaryl moiety. Three chiral centers are obtained from the starting material L-xylose, while the other two were established (or modified) via three highly stereoselective transformations: Luche reduction (dr: 97/3), dynamic kinetic resolution of anomeric hemiacetal (dr: 95/5), and Lewis acid-promoted thiolation (dr: 1000/ 1). Global deprotection of the resulting penultimate intermediate with catalytic sodium methoxide followed by recrystallization furnishes sotagliflozin. The longest linear sequence consists of 10 steps from L-xylose with an overall yield of 40%. This process has been performed on multi-hundred kilogram batches to satisfy the drug substance development demands.

Three compounds as well as preparations method and application thereof in synthesis of sotagliflozin

The invention provides compounds shown in formulas IV, V and VI as well as preparation methods of the compounds. The invention further provides application of the compounds shown in formulas IV, V andVI in synthesis of sotagliflozin. Raw materials related to the method are easy to obtain and low in price, and the method is simple and convenient to operate, saving, environmentally friendly and facilitates industrial production.

Radical Dehydroxymethylative Fluorination of Carbohydrates and Divergent Transformations of the Resulting Reverse Glycosyl Fluorides

A mild and convenient method for the synthesis of reverse glycosyl fluorides (RGFs) has been developed that is based on the silver-promoted radical dehydroxymethylative fluorination of carbohydrates. A salient feature of the reaction is that furanoid and pyranoid carbohydrates furnish structurally diverse RGFs bearing a wide variety of functional groups in good to excellent yields. Intramolecular hydrogen atom transfer experiments revealed that the reaction involves an underexploited radical fluorination that proceeds via β-fragmentation of sugar-derived primary alkoxyl radicals. Structurally divergent RGFs were obtained by catalytic C?F bond activation, and our method thus offers a concise and efficient strategy for the synthesis of reverse glycosides by late-stage diversification of RGFs. The potential of this method is showcased by the preparation and diversification of sotagliflozin, leading to the discovery of a promising SGLT2 inhibitor candidate.

Synthetic method for sotagliflozin and its analogues

The invention discloses a synthetic method for sotagliflozin and its analogues. The method comprises the following steps: with dapagliflozin acetate 1 as a raw material, carrying out oxidation so as to obtain diaryl ketone 2; selectively removing an acetyl group in the compound 2 so as to obtain primary alconol 3; carrying out dehydroxymethyl fluorination so as to obtain fluoroglucoside 4; then subjecting a carbonyl group to reductive alkylation so as to obtain a compound 5; reacting an activated C-F bond and a nucleophilic reagent to obtain a glycosylation product 6a-6c; and finally removingan acetyl group so as to obtain sotagliflozin and its analogue 7a-7c, or subjecting the compound 5 to removal of the acetyl group to obtain a sotagliflozin analogue 7d. The synthetic method of the invention has the following advantages: the raw material dapagliflozin acetate can be prepared from inexpensive and easily available 1,5-gluconolactone; only the acetyl group is used as a protecting group which can be removed under mild conditions; a reducing agent sodium borohydride used in the method is cheap, easily available, and stable in water and air; stereoselective reduction is not involved,so the difficulty of synthesis is lowered, experimental operation is simplified, and the method is suitable for large-scale preparation.

Glucopyranosyl derivative and application thereof in medicine

The invention relates to a glucopyranosyl derivative as a sodium-dependent glucose transporter (SGLT) inhibitor, a pharmaceutical composition containing the derivative and an application thereof in medicine, and in particular to the glucopyranosyl derivative as shown in a formula (I) or a pharmaceutically acceptable salt or all stereisomers thereof, or use of the pharmaceutical composition containing the derivative and the derivative and the pharmaceutical composition for preparing medicines treating diabetes and diabetes related diseases.

COMPOSITIONS COMPRISING AND METHODS OF USING INHIBITORS OF SODIUM-GLUCOSE COTRANSPORTERS 1 AND 2

Pharmaceutical dosage forms useful for improving the cardiovascular and/or metabolic health of patients, particularly those suffering from type 2 diabetes, are disclosed, as well as methods of their manufacture.

Solid forms of (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol and methods of their use

Solid forms of anhydrous (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol are disclosed, in addition to methods of their use in the treatment of various diseases and disorders.

INHIBITORS OF SODIUM GLUCOSE CO-TRANSPORTER 2 AND METHODS OF THEIR USE

Compounds and pharmaceutical compositions comprising them are disclosed that may be useful for the treatment of diseases and disorders such as diabetes and obesity.