3-(3-[1-(tert-butoxycarbonyl)piperidine-4-carboxamido]-2-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}phenoxy)propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Base Information

• Chemical Name: 3-(3-[1-(tert-butoxycarbonyl)piperidine-4-carboxamido]-2-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}phenoxy)propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• CAS No.: 1402905-83-2
• Molecular Formula: C₄₂H₅₂ClN₃O₁₆S
• Molecular Weight: 922.404
• Mol file: 1402905-83-2.mol

Synonyms:

Chemical Property of 3-(3-[1-(tert-butoxycarbonyl)piperidine-4-carboxamido]-2-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}phenoxy)propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(3-[1-(tert-butoxycarbonyl)piperidine-4-carboxamido]-2-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}phenoxy)propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

There total 6 articles about 3-(3-[1-(tert-butoxycarbonyl)piperidine-4-carboxamido]-2-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}phenoxy)propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 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:

3-(2-amino-3-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}phenoxy)propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1402905-81-0) + N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid (84358-13-4,174286-31-8) → 3-(3-[1-(tert-butoxycarbonyl)piperidine-4-carboxamido]-2-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}phenoxy)propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1402905-83-2)

Guidance literature:

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid; With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 ℃; for 0.5h;

3-(2-amino-3-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}phenoxy)propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside; In tetrahydrofuran; at 20 ℃; for 48h;

DOI:10.1002/cmdc.201200224

Reference yield:

3-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}-2-nitrophenol (1402905-79-6) → 3-(3-[1-(tert-butoxycarbonyl)piperidine-4-carboxamido]-2-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}phenoxy)propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1402905-83-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h

1.2: 20 °C

2.1: tin(II) chloride dihdyrate / ethyl acetate / 48 h / Reflux

3.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / tetrahydrofuran / 0.5 h / 0 °C

3.2: 48 h / 20 °C

With tin(II) chloride dihdyrate; potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/cmdc.201200224

Reference yield:

3-(bromomethyl)-5-(5-chlorothiophen-2-yl)isoxazole (323594-39-4) → 3-(3-[1-(tert-butoxycarbonyl)piperidine-4-carboxamido]-2-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}phenoxy)propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1402905-83-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h

1.2: 20 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h

2.2: 20 °C

3.1: tin(II) chloride dihdyrate / ethyl acetate / 48 h / Reflux

4.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / tetrahydrofuran / 0.5 h / 0 °C

4.2: 48 h / 20 °C

With tin(II) chloride dihdyrate; potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/cmdc.201200224

upstream raw materials:

3-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}-2-nitrophenol

3-(2-amino-3-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}phenoxy)propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

β-D-glucose pentaacetate

Downstream raw materials:

3-(2-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}-3-[1-(isopropyl)piperidine-4-carboxamido]phenoxy)propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

3-(2-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}-3-[1-(isopropyl)piperidine-4-carboxamido]phenoxy)propyl β-D-glucopyranoside

3-(3-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methoxy}-2-(piperidine-4-carboxamido)phenoxy)propyl β-D-glucopyranoside