Atigliflozin

Base Information

• Chemical Name: Atigliflozin
• CAS No.: 647834-15-9
• Deprecated CAS: 897656-44-9,1337352-23-4
• Molecular Formula: C18H22O7S
• Molecular Weight: 382.43
• UNII: Y0H7UPE4WJ
• Wikidata: Q27294103
• NCI Thesaurus Code: C91017
• Mol file: 647834-15-9.mol

Synonyms:AVE2268

Chemical Property of Atigliflozin

Chemical Property:

• PSA: 136.85000
• LogP: 0.52620
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 382.10862421
• Heavy Atom Count: 26
• Complexity: 432

Purity/Quality:

98% ^*data from raw suppliers

ATIGLIFLOZIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)CC2=C(C=CS2)OC3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: COC1=CC=C(C=C1)CC2=C(C=CS2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• Recent ClinicalTrials: Dose-Ranging Study Evaluating AVE2268 in Patients With Type 2 Diabetes Not Adequately Controlled by a Metformin Treatment
• Recent EU Clinical Trials: A randomized, double-blind, parallel-group, placebo-controlled, dose-response, multicentre, multinational study evaluating the efficacy and safety of AVE2268 administered either twice daily (breakfast and lunch) at a dose of 300, 600 and 1200 mg or once daily (breakfast) at a dose of 1200 mg, in patients with type 2 diabetes treated with metformin and not adequately controlled

Technology Process of Atigliflozin

There total 3 articles about Atigliflozin 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: 83.0%

4,5-diacetoxy-6-acetoxymethyl-2-[2-(4-methoxybenzyl)thiophen-3-yloxy]tetrahydropyran-3-yl acetate → 2-Hydroxymethyl-6-[2-(4-methoxybenzyl)thiophen-3-yloxy]tetrahydropyran-3,4,5-triol (647834-15-9)

Guidance literature:

4,5-diacetoxy-6-acetoxymethyl-2-[2-(4-methoxybenzyl)thiophen-3-yloxy]tetrahydropyran-3-yl acetate; With sodium methylate; In methanol; at 0 ℃; for 1.5h;

With acetic acid; In methanol; pH=7;

Reference yield:

2-{2-[hydroxy-(4-methoxy-phenyl)-methyl]-thiophen-3-yloxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol → Atigliflozin (647834-15-9)

Guidance literature:

With hydrogen; palladium over charcoal; In ethanol; at 22 ℃; for 6 - 7h;

Reference yield:

acetic acid 3,4,5-triacetoxy-6-[2-(4-methoxy-benzyl)-thiophen-3-yloxy]-tetrahydro-pyran-2-yl-methyl ester (897656-37-0) → Atigliflozin (647834-15-9)

Guidance literature:

acetic acid 3,4,5-triacetoxy-6-[2-(4-methoxy-benzyl)-thiophen-3-yloxy]-tetrahydro-pyran-2-yl-methyl ester; With chloro-trimethyl-silane; sodium cyanoborohydride; In acetonitrile; at 0 ℃; for 2h;

With sodium methylate; In methanol; at 22 ℃; for 18h;

In methanol;

upstream raw materials:

acetic acid 3,4,5-triacetoxy-6-[2-(4-methoxy-benzyl)-thiophen-3-yloxy]-tetrahydro-pyran-2-yl-methyl ester

Downstream raw materials:

3-O-(2-(4-methoxybenzyl)thiophenyl)-6-O-(tert-butyldiphenylsilyl)-3,4,5-tri-O-acetyl-β-D-glucopyranoside

3-O-(2-(4-methoxybenzyl)thiophenyl)-3,4,5-tri-O-acetyl-β-D-glucuronide

3-O-(2-(4-methoxybenzyl)-thiophenyl)-β-D-3,4,5-tri-O-acetyl-glucopyranoside

3-(2-(4-methoxybenzyl)-thiophenyl)-β-D-glucuronide

Refernces

• 1、 -. "NOVEL THIOPHENYLGLYCOSIDE DERIVATIVES, METHODS FOR PRODUCTION THEREOF, MEDICAMENTS COMPRISING SAID COMPOUNDS AND USE THEREOF". Page/Page column 43-44. . Retrieved 2010/11/30.