(3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 461432-24-6
• Molecular Formula: C29H33ClO10
• Molecular Weight: 438.905
• DSSTox Substance ID: DTXSID601148940
• Mol file: 461432-24-6.mol

Synonyms:461432-24-6;(3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol;Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucopyranoside;SCHEMBL1551581;GKTWLVVOULBRDU-VEIQOZLZSA-N;DTXSID601148940;CS-13058;CS-0009474;D-Glucopyranoside,Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-;Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]d-glucopyranoside;D-Glucopyranoside, Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-;(3R,4S,5S,6R)-2-(3-(4-ethoxybenzyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxy-tetrahydro-2H-pyran-3,4,5-triol;(3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxyoxane-3,4,5-triol

Chemical Property of (3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

• Boiling Point: 609.6±55.0 °C(Predicted)
• PKA: 12.59±0.70(Predicted)
• PSA: 108.61000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 1.60250
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 438.1445309
• Heavy Atom Count: 30
• Complexity: 530

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)C3(C(C(C(C(O3)CO)O)O)O)OC)Cl
• Isomeric SMILES: CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)C3([C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC)Cl
• Use Description: (3R,4R,5R,6S)-2-(acetoxyMethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate is a complex chemical compound with potential applications across various fields. In the pharmaceutical industry, it might be utilized as a critical intermediate or precursor in the synthesis of pharmaceutical drugs, potentially playing a role in the development of medications with therapeutic applications. In the field of organic chemistry and chemical synthesis, this compound can be employed as a versatile building block for the creation of complex organic molecules, aiding in the development of novel chemical compounds. Additionally, in biochemical research and studies related to molecular biology, it may find use as a tool for investigating cellular processes and molecular interactions, supporting advancements in scientific research. Its adaptability as a pharmaceutical intermediate, chemical building block, and research tool underscores its significance in advancing drug development, organic chemistry, and scientific understanding in various fields.

Technology Process of (3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

There total 20 articles about (3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 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: 99.0%

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene (461432-23-5) + (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (32469-28-6,55515-28-1,55515-29-2,32384-65-9) → (3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (461432-24-6)

Guidance literature:

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene; With n-butyllithium; isopropylmagnesium chloride; In tetrahydrofuran; hexane; toluene; at -30 ℃; for 1h;

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; hexane; toluene; for 1h;

Reference yield: 90.0%

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene (1103738-29-9) + (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (32469-28-6,55515-28-1,55515-29-2,32384-65-9) → (3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (461432-24-6)

Guidance literature:

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene; With TurboGrignard; In tetrahydrofuran; at -5 - 0 ℃; for 2h; Inert atmosphere;

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; n-heptane; at -5 - 0 ℃; for 2h;

With hydrogenchloride; In tetrahydrofuran; methanol; n-heptane; at 0 - 20 ℃; for 16h;

Reference yield: 64.3%

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene (461432-23-5) + methanesulfonic acid (75-75-2,98527-29-8) + (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (32469-28-6,55515-28-1,55515-29-2,32384-65-9) → (3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (461432-24-6)

Guidance literature:

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -72 - -60 ℃; for 2h; Inert atmosphere;

methanesulfonic acid; In methanol; at 20 ℃;

upstream raw materials:

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

methanol

C₃₃H₅₇ClO₇Si₄

Downstream raw materials:

(1S)-1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Refernces

• 1、 -. "AMORPHOUS ERTUGLIFLOZIN AND PROCESS FOR ITS PREPARATION". Paragraph 0065; 0137; 0138. . Retrieved 2020/12/13.
• 2、 -. "Dicyclic derivative of glucoside as well as preparation method and application of dicyclic derivative". . . Retrieved 2018/07/30.