EGT1442

Base Information

• Chemical Name: EGT1442
• CAS No.: 1118567-05-7
• Molecular Formula: C24H29ClO7
• Molecular Weight: 464.943
• Mol file: 1118567-05-7.mol

Synonyms:EGT1442;(1S)-1,5-Anhydro-1-C-[4-chloro-3-[[4-[2-(cyclopropyloxy)ethoxy]phenyl]methyl]phenyl]-D-glucitol;Bexagliflozin

Chemical Property of EGT1442

Chemical Property:

• Boiling Point: 671.0±55.0 °C(Predicted)
• PKA: 13.23±0.70(Predicted)
• PSA: 108.61000
• Density: 1.41
• LogP: 2.00350

Purity/Quality:

98%,99%, ^*data from raw suppliers

Bexagliflozin3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: EGT-1442 is a potent, selective sodium glucose co-transporter 2 (SGLT2) inhibitor with IC50 values of 5.6 μM and 2 nM for human SGLT1 and SGLT2, respectively. It produces a stable urinary excretion of glucose in rats and dogs with ED50 values of 0.38 and 0.09 mg/kg, respectively, and reduces HbA(1c) and blood glucose in db/db mice in a concentration dependent manner.
• Uses: Bexagliflozin, also known as EGT1442, is a potent and selective SGLT2 inhibitor, attenuates blood glucose and HbA(1c) levels in db/db mice and prolongs the survival of stroke-prone rats. EGT1442 showed favorable properties both in vitro and in vivo and could be beneficial to the management of type 2 diabetic patients.

Technology Process of EGT1442

There total 24 articles about EGT1442 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: 93.9%

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, bis(L-proline) complex → (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1118567-05-7)

Guidance literature:

In methanol; water; at 20 ℃; for 5h; Product distribution / selectivity;

Reference yield: 90.0%

(3R,4S,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (1459754-30-3) → (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1118567-05-7)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile; at -25 - -20 ℃; for 4h; Temperature; Concentration; Inert atmosphere; Large scale;

Reference yield:

(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone (461432-22-4) → (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1118567-05-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylsilane; trifluorormethanesulfonic acid; trifluoroacetic acid / 20 °C / Reflux

2.1: n-butyllithium / tetrahydrofuran; toluene / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C

3.1: triethylsilane; boron trifluoride diethyl etherate / methanol; dichloromethane / 0 °C

4.1: boron tribromide / dichloromethane / -78 - 0 °C

5.1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C

With triethylsilane; n-butyllithium; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; boron tribromide; caesium carbonate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

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

2-(cyclopropyloxy)ethyl-4-methylbenzenesulfonate

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[[4-[2-(cyclopropyloxy)ethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)-2-methoxytetrahydropyran-3,4,5-triol

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

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF BENZYLBENZENE SGLT2 INHIBITORS". Paragraph 0281; 0282. . Retrieved 2013/10/22.
• 2、 -. "PROCESS FOR PREPARATION OF BENZYLBENZENE SODIUM-DEPENDENT GLUCOSE COTRANSPORTER 2 (SGLT2) INHIBITORS". Paragraph 0234; 0235. . Retrieved 2013/11/05.