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

Base Information

• Chemical Name: (2S,4R)-tert-butyl-2-(tert-butoxycarbonylamino)-4-hydroxy-5-oxo-5-(2,4,6-trimethoxybenzylamino)pentanoate
• CAS No.: 1262523-64-7
• Molecular Formula: C₂₄H₃₈N₂O₉
• Molecular Weight: 498.574
• Mol file: 1262523-64-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (2S,4R)-tert-butyl-2-(tert-butoxycarbonylamino)-4-hydroxy-5-oxo-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:

(2S)-tert-butyl-2-(tert-butoxycarbonylamino)-4-(2-chloroacetoxy)-5-oxo-5-(2,4,6-trimethoxybenzylamino)pentanoate (1262523-46-5) → (2S,4R)-tert-butyl-2-(tert-butoxycarbonylamino)-4-hydroxy-5-oxo-5-(2,4,6-trimethoxybenzylamino)pentanoate (1262523-64-7) + (2S,4S)-tert-butyl-2-(tert-butoxycarbonylamino)-4-hydroxy-5-oxo-5-(2,4,6-trimethoxybenzylamino)pentanoate (1262523-62-5)

Guidance literature:

With sodium hydrogencarbonate; thiourea; In tetrahydrofuran; ethanol; at 50 ℃; for 1.5h;

DOI:10.1021/ja109203d

Reference yield:

2-(isocyanomethyl)-1,3,5-trimethoxybenzene (480438-26-4) → (2S,4R)-tert-butyl-2-(tert-butoxycarbonylamino)-4-hydroxy-5-oxo-5-(2,4,6-trimethoxybenzylamino)pentanoate (1262523-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 24 h / 20 °C

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

With sodium hydrogencarbonate; thiourea; In tetrahydrofuran; ethanol; dichloromethane; 1: Passerini reaction;

DOI:10.1021/ja109203d

Reference yield:

N-(2,4,6-trimethoxybenzyl)formamide (1112292-12-2) → (2S,4R)-tert-butyl-2-(tert-butoxycarbonylamino)-4-hydroxy-5-oxo-5-(2,4,6-trimethoxybenzylamino)pentanoate (1262523-64-7)

Guidance literature:

Multi-step reaction with 3 steps

1: phosgene; triethylamine / dichloromethane / 0 - 20 °C

2: dichloromethane / 24 h / 20 °C

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

With phosgene; sodium hydrogencarbonate; triethylamine; thiourea; In tetrahydrofuran; ethanol; dichloromethane; 2: Passerini reaction;

DOI:10.1021/ja109203d

upstream raw materials:

2-(isocyanomethyl)-1,3,5-trimethoxybenzene

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

N-(2,4,6-trimethoxybenzyl)formamide

BOC-L-aspartic acid 4-benzyl ester

Downstream raw materials:

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

C₂₄H₃₇⁽¹⁸⁾FN₂O₈

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