di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-({5-[3-(tosyloxy)propyl]pyridin-2-yl}methyl)-L-glutamate

Base Information

• Chemical Name: di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-({5-[3-(tosyloxy)propyl]pyridin-2-yl}methyl)-L-glutamate
• CAS No.: 1407506-52-8
• Molecular Formula: C₃₄H₅₀N₂O₉S
• Molecular Weight: 662.845
• Mol file: 1407506-52-8.mol

Synonyms:di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-({5-[3-(tosyloxy)propyl]pyridin-2-yl}methyl)-L-glutamate

Chemical Property of di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-({5-[3-(tosyloxy)propyl]pyridin-2-yl}methyl)-L-glutamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-({5-[3-(tosyloxy)propyl]pyridin-2-yl}methyl)-L-glutamate

There total 6 articles about di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-({5-[3-(tosyloxy)propyl]pyridin-2-yl}methyl)-L-glutamate 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: 44.8%

p-toluenesulfonylanhydride (4124-41-8) + Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(3-hydroxypropyl)pyridin-2-yl]methyl}-L-glutamate (1407507-47-4) → di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-({5-[3-(tosyloxy)propyl]pyridin-2-yl}methyl)-L-glutamate (1407506-52-8)

Guidance literature:

With triethylamine; dmap; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

di-tert-butyl (N-tert-butoxycarbonyl)-L-glutamate → di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-({5-[3-(tosyloxy)propyl]pyridin-2-yl}methyl)-L-glutamate (1407506-52-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C

1.2: 3 h

2.1: potassium carbonate / triphenylphosphine; palladium diacetate / 1,2-dimethoxyethane; water / 16.5 h / 80 °C / Inert atmosphere

3.1: hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C

4.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0 °C

5.1: triethylamine / dmap / dichloromethane / 2 h / 20 °C

With tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; acetic acid; triethylamine; lithium hexamethyldisilazane; dmap; palladium 10% on activated carbon; palladium diacetate; triphenylphosphine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water;

Reference yield:

di-tert-butyl (4R)-4-[(5-bromopyridin-2-yl)methyl]-N-(tert-butoxycarbonyl)-L-glutamate (1407507-23-6) → di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-({5-[3-(tosyloxy)propyl]pyridin-2-yl}methyl)-L-glutamate (1407506-52-8)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / triphenylphosphine; palladium diacetate / 1,2-dimethoxyethane; water / 16.5 h / 80 °C / Inert atmosphere

2: hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C

3: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0 °C

4: triethylamine / dmap / dichloromethane / 2 h / 20 °C

With tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; acetic acid; triethylamine; dmap; palladium 10% on activated carbon; palladium diacetate; triphenylphosphine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water;

upstream raw materials:

5-bromo-2-(bromomethyl)pyridine

di-tert-butyl (4R)-4-[(5-bromopyridin-2-yl)methyl]-N-(tert-butoxycarbonyl)-L-glutamate

di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-({5-[(E)-3-{[tert-butyl(dimethyl)silyl]oxy}prop-1-en-1-yl]pyridin-2-yl}methyl)-L-glutamate

Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(3-{[tert-butyl(dimethyl)silyl]-oxy}propyl)pyridin-2-yl]methyl}-L-glutamate