(2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 1620758-33-9
• Molecular Formula: C₂₃H₂₇ClO₇
• Molecular Weight: 450.916
• UNII: 2B7SR85N8B
• Nikkaji Number: J3.321.733A
• Mol file: 1620758-33-9.mol

Synonyms:1620758-33-9;Empagliflozin alpha-Anomer;(2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;2B7SR85N8B;(2R,3R,4R,5S,6R)-2-[4-chloro-3-[[4-[(3S)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol;(1R)-1,5-Anhydro-1-C-(4-chloro-3-((4-(((3S)-tetrahydro-3-furanyl)oxy)phenyl)methyl)phenyl)-D-glucitol;D-Glucitol, 1,5-anhydro-1-C-(4-chloro-3-((4-(((3S)-tetrahydro-3-furanyl)oxy)phenyl)methyl)phenyl)-, (1R)-;UNII-2B7SR85N8B;Empagliflozin +/--Anomer-d4;OBWASQILIWPZMG-DNNBANOASA-N;VPC75833;EMPAGLIFLOZIN .ALPHA.-ANOMER;CS-0165372;(2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol? (Empagliflozin Impurity pound(c);(2R,3S,4R,5R,6R)-6-{4-chloro-3-[(4-{[(3S)-tetrahydro-3-furyl]oxy}phenyl)methyl]phenyl}-2-(hydroxymethyl)tetrahydropyran-3,4,5-triol;1-[3-[4-[[(3S)-Tetrahydrofuran-3-yl]oxy]benzyl]-4-chlorophenyl]-1-deoxy-alpha-D-glucopyranose

Chemical Property of (2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

• Boiling Point: 664.5±55.0 °C(Predicted)
• PKA: 13.23±0.70(Predicted)
• Density: 1.398±0.06 g/cm3(Predicted)
• XLogP3: 2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 450.1445309
• Heavy Atom Count: 31
• Complexity: 558

Purity/Quality:

99%+, ^*data from raw suppliers

Empagliflozinα-Anomer ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1COCC1OC2=CC=C(C=C2)CC3=C(C=CC(=C3)C4C(C(C(C(O4)CO)O)O)O)Cl
• Isomeric SMILES: C1COC[C@H]1OC2=CC=C(C=C2)CC3=C(C=CC(=C3)[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)Cl
• Uses: Empagliflozin α-Anomer is a derivative of Empagliflozin (E521510), a novel, potent and selective SGLT-2 inhibitor, improves glycaemic control syndrome in diabetic rats.

Technology Process of (2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

There total 156 articles about (2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-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: 93.8%

C29H32BrClO9 → empagliflozin (864070-44-0,1620758-33-9,864070-43-9)

Guidance literature:

With water; potassium hydroxide; In acetonitrile; at 50 - 60 ℃; Reagent/catalyst;

Reference yield: 93.7%

C51H49ClO7 → empagliflozin (864070-44-0,1620758-33-9,864070-43-9)

Guidance literature:

With hydrogen; In ethanol; at 75 - 80 ℃; for 20h; under 6000.6 - 6750.68 Torr; Solvent; Inert atmosphere; Autoclave;

Reference yield: 90.0%

C51H43ClO11 → empagliflozin (864070-44-0,1620758-33-9,864070-43-9)

Guidance literature:

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

upstream raw materials:

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

toluene-4-sulfonic acid (S)-(tetrahydrofuran-3-yl)ester

1-chloro-4-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-2-(4-(R)-tetrahydrofuran-3-yloxy-benzyl)-benzene

(R)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate

Refernces

• 1、 -. "Preparation method of SGLT-2 inhibitor and intermediate". . . Retrieved 2021/05/19.
• 2、 -. "Synthetic method of empagliflozin". Paragraph 0039; 0041-0042; 0044. . Retrieved 2021/10/30.