1528636-39-6

Basic information

• Product Name: (2S,3R,4S,5S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
• Synonyms: (2S,3R,4S,5S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol;Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-5-C-(hydroxymethyl)-alpha-D-xylo-hexopyranoside;α-D-xylo-Hexopyranoside,methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-5-C-(hydroxymethyl)-
• CAS NO: 1528636-39-6
• Molecular Formula: C₂₃H₂₉ClO₈
• Molecular Weight: 468.92456
• EINECS: -0
• Mol File: 1528636-39-6.mol

Chemical Properties

• Boiling Point: 651.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.42±0.1 g/cm3(Predicted)
• PKA: 12.47±0.70(Predicted)
• CAS DataBase Reference: (2S,3R,4S,5S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4S,5S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol(1528636-39-6)
• EPA Substance Registry System: (2S,3R,4S,5S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol(1528636-39-6)

Safety Data

• Hazardous Substances Data: 1528636-39-6(Hazardous Substances Data)

Usage

Uses

(2S,3R,4S,5S)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol is an antidiabetic agent and an Ertugliflozin (1210344-57-2) intermediate.

Upstream product

• 50-00-0 formaldehyd 
• 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 
• 1528636-29-4 ((2R,3R,4S,5R,6S)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-methoxy-3,4,5-tris-(trimethylsilyloxy)tetrahydro-2H-pyran-2-yl)methanol 
• 1528636-33-0 (2S,3R,4S,5R,6S)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-methoxy-3,4,5-tris-(trimethylsilyloxy)tetrahydro-2H-pyran-2-carbaldehyde 
• 714269-57-5 (2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 
• 1528636-28-3 C₃₄H₅₉ClO₇Si₄ 

Downstream Products

• 1210344-57-2 Ertugliflozin 
• 1210344-83-4 (1S,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (1:1) compound with (S)-5-oxopyrrolidine-2-carboxylic acid 

Relevant articles and documents

AN EFFICIENT PROCESS FOR THE PREPARATION OF ERTUGLIFLOZIN L-PYROGLUTAMIC ACID AND INTERMEDIATES THEREOF

The present invention relates to an efficient process for the preparation of Ertugliflozin L-pyroglutamic acid of formula (I) and intermediate thereof, in environment friendly conditions. The present invention further relates to a process for the preparation of substantially pure intermediate of formula (IV).

Preparation method of synthesis ertugliflozin intermediate

The invention discloses a preparation method of a synthesis ertugliflozin ( Ertugliflozin, compound VII) intermediate as shown in a formula I. The Ertugliflozin is a medicine for treating diabetes mellitus type 2, jointly developed by Merck and Pfizer, and is a bran-new glucose sodium transport protein inhibitor(SGLT-2). The invention provides a preparation route method, and the method has the defects of being long in route, high in analysis difficulty, low in yield and the like. The preparation method comprises the following steps of protecting the compound II with TMS, performing oxidation,and performing disproportionation to generate a compound I. The preparation method for synthesis of the compound I is high in yield, simple and convenient to operate and low in cost, and is suitable for industrial mass production. A new way is provided for preparation of the ertugliflozin.

Development of an early-phase bulk enabling route to sodium-dependent glucose cotransporter 2 inhibitor ertugliflozin

The development and optimization of a scalable synthesis of sodium-dependent glucose cotransporter 2 inhibitor, ertugliflozin, for the treatment of type-2 diabetes is described. Highlights of the chemistry are a concise, four-step synthesis of a structurally complex API from known intermediate 4 via persilylation-selective monodesilylation, primary alcohol oxidation, aldol-crossed-Cannizzaro reaction, and solid-phase acid-catalyzed bicyclic ketal formation. The final API was isolated as the Lpyroglutamic acid cocrystal.