(1S)-1,5-anhydro-2,3,4,6-tetra-O-acteyl-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydrofu-ran-3-yl]oxy]phenyl] methyl]phenyl]-D-Glucitol

Base Information

• Chemical Name: (1S)-1,5-anhydro-2,3,4,6-tetra-O-acteyl-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydrofu-ran-3-yl]oxy]phenyl] methyl]phenyl]-D-Glucitol
• CAS No.: 915095-99-7
• Molecular Formula: C₃₁H₃₅ClO₁₁
• Molecular Weight: 619.065
• Mol file: 915095-99-7.mol

Synonyms:(1S)-1,5-anhydro-2,3,4,6-tetra-O-acteyl-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydrofu-ran-3-yl]oxy]phenyl] methyl]phenyl]-D-Glucitol;Acetoxy Empagliflozin;(1S)-1,5-Anhydro-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-D-glucitol tetraacetate

Chemical Property of (1S)-1,5-anhydro-2,3,4,6-tetra-O-acteyl-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydrofu-ran-3-yl]oxy]phenyl] methyl]phenyl]-D-Glucitol

Chemical Property:

• Boiling Point: 673.8±55.0 °C(Predicted)
• PSA: 132.89000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 3.89660

Purity/Quality:

99%, ^*data from raw suppliers

Peracetyl Empagliflozin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Acetoxy Empagliflozin can be used as Empagliflozin intermediates and pharmaceutical intermediates, mainly used in laboratory research and development processes and chemical production processes. Impurity of the drug Empagliflozin (E521510). From process for the preparation of glucopyranosyl-substituted benzonitriles for use as therapeutic agents treating metabolic disorders.

Technology Process of (1S)-1,5-anhydro-2,3,4,6-tetra-O-acteyl-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydrofu-ran-3-yl]oxy]phenyl] methyl]phenyl]-D-Glucitol

There total 70 articles about (1S)-1,5-anhydro-2,3,4,6-tetra-O-acteyl-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydrofu-ran-3-yl]oxy]phenyl] methyl]phenyl]-D-Glucitol 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: 92.6%

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3) + (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene (915095-89-5) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-trityl triacetate (915095-99-7)

Guidance literature:

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene; With n-butyllithium; isopropyl magnesium chloride - lithium chloride complex; In tetrahydrofuran; hexane; at -10 ℃; for 2h; Inert atmosphere;

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide; In tetrahydrofuran; hexane; at -10 ℃; for 3h; Inert atmosphere;

With methanesulfonic acid; In tetrahydrofuran; methanol; hexane; at 25 ℃; for 18h; Reagent/catalyst; Inert atmosphere;

Reference yield: 91.0%

empagliflozin (864070-44-0,1620758-33-9,864070-43-9) + acetic anhydride (108-24-7) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-trityl triacetate (915095-99-7)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 4h;

Reference yield: 90.0%

(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran (915095-94-2) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 1-chloro-4-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-2-(4-(R)-tetrahydrofuran-3-yloxy-benzyl)-benzene (915095-98-6,915095-99-7)

Guidance literature:

With bis(acetylacetonate)nickel(II); magnesium chloride; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; zinc; In tetrahydrofuran; at 20 ℃; Schlenk technique; Inert atmosphere; Cooling with ice;

upstream raw materials:

1-chloro-4-(1-methoxy-D-glucopyranos-1-yl)-2-(4-(R)-tetrahydrofuran-3-yloxy-benzyl)-benzene

(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

empagliflozin

Refernces

• 1、 -. "Synthetic method of empagliflozin". . . Retrieved 2020/02/14.
• 2、 -. "Synthesizing method suitable for industrial empagliflozin production". . . Retrieved 2019/10/17.