di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{4-[3-(tosyloxy)propyl]benzyl}-L-glutamate

Base Information

Chemical Name:di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{4-[3-(tosyloxy)propyl]benzyl}-L-glutamate
CAS No.:1407506-24-4
Molecular Formula:C₃₅H₅₁NO₉S
Molecular Weight:661.857
Hs Code.:

Synonyms:di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{4-[3-(tosyloxy)propyl]benzyl}-L-glutamate

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Chemical Property of di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{4-[3-(tosyloxy)propyl]benzyl}-L-glutamate

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Technology Process of di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{4-[3-(tosyloxy)propyl]benzyl}-L-glutamate

There total 6 articles about di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{4-[3-(tosyloxy)propyl]benzyl}-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: 26.7%

: 4124-41-8
p-toluenesulfonylanhydride

: 1407507-18-9
di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-[4-(3-hydroxypropyl)benzyl]-L-glutamate

: 1407506-24-4
di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{4-[3-(tosyloxy)propyl]benzyl}-L-glutamate

Guidance literature:: With pyridine; at 0 ℃; for 2h;

Reference yield:

: 433332-03-7
1-(3-benzyloxypropyl)-4-bromobenzene

: 1407506-24-4
di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{4-[3-(tosyloxy)propyl]benzyl}-L-glutamate

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -75 °C / Inert atmosphere

1.2: 0.5 h

2.1: ethanol; sodium tetrahydroborate / 1 h / 20 °C

3.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h / 0 °C

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

4.2: 2 h

5.1: hydrogen / palladium 10% on activated carbon / methanol / 20 °C

6.1: pyridine / 2 h / 0 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; ethanol; carbon tetrabromide; hydrogen; triphenylphosphine; lithium hexamethyldisilazane; palladium 10% on activated carbon; In tetrahydrofuran; methanol; hexane; dichloromethane;

Reference yield:

: 770745-89-6
4-[3-(benzyloxy)propyl]benzaldehyde

: 1407506-24-4
di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{4-[3-(tosyloxy)propyl]benzyl}-L-glutamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: ethanol; sodium tetrahydroborate / 1 h / 20 °C

2.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h / 0 °C

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

3.2: 2 h

4.1: hydrogen / palladium 10% on activated carbon / methanol / 20 °C

5.1: pyridine / 2 h / 0 °C

With pyridine; sodium tetrahydroborate; ethanol; carbon tetrabromide; hydrogen; triphenylphosphine; lithium hexamethyldisilazane; palladium 10% on activated carbon; In tetrahydrofuran; methanol; dichloromethane;