(2S)-tert-butyl-2-(tert-butoxycarbonylamino)-5-oxo-4-(tosyloxy)-5-(2,4,6-trimethoxybenzylamino)pentanoate

Base Information

• Chemical Name: (2S)-tert-butyl-2-(tert-butoxycarbonylamino)-5-oxo-4-(tosyloxy)-5-(2,4,6-trimethoxybenzylamino)pentanoate
• CAS No.: 1262523-50-1
• Molecular Formula: C₃₁H₄₄N₂O₁₁S
• Molecular Weight: 652.763
• Mol file: 1262523-50-1.mol

Synonyms:(2S)-tert-butyl-2-(tert-butoxycarbonylamino)-5-oxo-4-(tosyloxy)-5-(2,4,6-trimethoxybenzylamino)pentanoate

Chemical Property of (2S)-tert-butyl-2-(tert-butoxycarbonylamino)-5-oxo-4-(tosyloxy)-5-(2,4,6-trimethoxybenzylamino)pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-tert-butyl-2-(tert-butoxycarbonylamino)-5-oxo-4-(tosyloxy)-5-(2,4,6-trimethoxybenzylamino)pentanoate

There total 10 articles about (2S)-tert-butyl-2-(tert-butoxycarbonylamino)-5-oxo-4-(tosyloxy)-5-(2,4,6-trimethoxybenzylamino)pentanoate 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: 96.0%

(2S)-tert-butyl 2-(tert-butoxycarbonylamino)-4-hydroxy-5-oxo-5-(2,4,6-trimethoxybenzylamino)pentanoate (1262523-48-7) + p-toluenesulfonyl chloride (98-59-9) → (2S)-tert-butyl-2-(tert-butoxycarbonylamino)-5-oxo-4-(tosyloxy)-5-(2,4,6-trimethoxybenzylamino)pentanoate (1262523-50-1)

Guidance literature:

With triethylamine; dmap; In dichloromethane; at 0 - 20 ℃;

Reference yield:

2,4,6-trimethoxybenzylamine (77648-20-5) → (2S)-tert-butyl-2-(tert-butoxycarbonylamino)-5-oxo-4-(tosyloxy)-5-(2,4,6-trimethoxybenzylamino)pentanoate (1262523-50-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 h / 20 °C

2: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 20 °C / Cooling with ice

3: dichloromethane / 24 h / 20 °C

4: thiourea; sodium hydrogencarbonate / ethanol; tetrahydrofuran / 1.5 h / 50 °C

5: triethylamine / dmap / dichloromethane / 0 - 20 °C

With bis(trichloromethyl) carbonate; sodium hydrogencarbonate; triethylamine; thiourea; dmap; In tetrahydrofuran; ethanol; dichloromethane; 3: Passerini Reaction;

Reference yield:

N-tert-butoxycarbonyl aspartic acid tert-butyl ester (34582-32-6) → (2S)-tert-butyl-2-(tert-butoxycarbonylamino)-5-oxo-4-(tosyloxy)-5-(2,4,6-trimethoxybenzylamino)pentanoate (1262523-50-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / -10 - -5 °C

1.2: 4 h / 20 °C / Cooling with ice

1.3: pH 2 - 3 / Cooling with ice

2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C

3.1: dichloromethane / 24 h / 20 °C

4.1: thiourea; sodium hydrogencarbonate / ethanol; tetrahydrofuran / 1.5 h / 50 °C

5.1: triethylamine / dmap / dichloromethane / 0 - 20 °C

With chloroformic acid ethyl ester; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; thiourea; dmap; In tetrahydrofuran; ethanol; dichloromethane; 3.1: Passerini Reaction;

upstream raw materials:

(2S)-tert-butyl 2-(tert-butoxycarbonylamino)-4-hydroxy-5-oxo-5-(2,4,6-trimethoxybenzylamino)pentanoate

p-toluenesulfonyl chloride

2,4,6-trimethoxybenzylamine

BOC-L-aspartic acid 4-benzyl ester