(2S,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: (2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxyMethyl)-2-Methoxytetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 714269-57-5
• Molecular Formula: C22H27ClO7
• Molecular Weight: 438.905
• Mol file: 714269-57-5.mol

Synonyms:(2S,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-ethoxybenzyl)phenyl]-α-D-glucopyranoside; Methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-alpha-D-glucopyranoside; methyl 1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-α-D-Glucopyranoside

Chemical Property of (2S,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 (20 oC 760 Torr)
• LogP: 1.60250
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

1α-MethylDapagliflozin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1α-Methyl Dapagliflozin is an antidiabetic agent and intermediate of Dapagliflozin (D226255]), a sodium-glucose transporter 2 inhibitor.

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

There total 39 articles about (2S,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: 81.8%

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) → (2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol (714269-57-5)

Guidance literature:

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; With TurboGrignard; In tetrahydrofuran; at -30 - -20 ℃; for 1h; Inert atmosphere;

With methanesulfonic acid; In tetrahydrofuran; methanol; at -10 - 30 ℃; for 2h; Inert atmosphere;

Reference yield: 81.4%

methanesulfonic acid (75-75-2,98527-29-8) + C33H56ClO7Si4(1-)*Li(1+) → (2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol (714269-57-5)

Guidance literature:

In methanol; at 20 ℃; for 10h;

Reference yield: 78.6%

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene (461432-23-5) + C18H42O6Si4 → (2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol (714269-57-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -78 - -65 ℃; for 2h; Inert atmosphere;

upstream raw materials:

methanol

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

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

2-chloro-5-iodobenzoylchloride

Downstream raw materials:

dapagliflozin

C₄H₆O₂*C₂₂H₂₇ClO₇

methyl-2,3,4,6-tetra-O-acetyl-1-C-(2-chloro-4'ethoxydiphenylmethan-3yl)-α-D-glucopyranose

((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

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