(S)-2-[N-tert-butoxycarbonyl-N-(4′-Methoxybenzyl)amino]-3-phenylpropionaldehyde

Base Information

• Chemical Name: (S)-2-[N-tert-butoxycarbonyl-N-(4′-Methoxybenzyl)amino]-3-phenylpropionaldehyde
• CAS No.: 169905-23-1
• Molecular Formula: C₂₂H₂₇NO₄
• Molecular Weight: 369.461
• Mol file: 169905-23-1.mol

Synonyms:(S)-2-[N-tert-butoxycarbonyl-N-(4′-Methoxybenzyl)amino]-3-phenylpropionaldehyde

Chemical Property of (S)-2-[N-tert-butoxycarbonyl-N-(4′-Methoxybenzyl)amino]-3-phenylpropionaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[N-tert-butoxycarbonyl-N-(4′-Methoxybenzyl)amino]-3-phenylpropionaldehyde

There total 7 articles about (S)-2-[N-tert-butoxycarbonyl-N-(4′-Methoxybenzyl)amino]-3-phenylpropionaldehyde 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: 83.0%

N-(tert-Butoxycarbonyl)-N-(4-methoxybenzyl)-L-phenylalaninol (169905-22-0) → (S)-2-[N-tert-butoxycarbonyl-N-(4′-Methoxybenzyl)amino]-3-phenylpropionaldehyde (169905-23-1)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b04129

Reference yield:

(2S)-2--3-phenyl-1-propanol (91373-74-9) → (S)-2-[N-tert-butoxycarbonyl-N-(4′-Methoxybenzyl)amino]-3-phenylpropionaldehyde (169905-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / dioxane

In 1,4-dioxane; 2: Swern oxidation;

DOI:10.1016/j.tetlet.2005.02.166

Reference yield:

4-methoxy-benzoyl chloride (100-07-2) → (S)-2-[N-tert-butoxycarbonyl-N-(4′-Methoxybenzyl)amino]-3-phenylpropionaldehyde (169905-23-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / LiAlH₄

2: 98 percent / dioxane

With lithium aluminium tetrahydride; In 1,4-dioxane; 4: Swern oxidation;

DOI:10.1016/j.tetlet.2005.02.166

upstream raw materials:

N-(tert-Butoxycarbonyl)-N-(4-methoxybenzyl)-L-phenylalaninol

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

4-methoxy-benzoyl chloride

(2S)-2--3-phenyl-1-propanol

Downstream raw materials:

(S,S)-2-<2--1-hydroxy-3-phenylpropyl>-1,3-thiazole

ethyl (4S,2Z)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate

ethyl (4S,2E)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-2-methyl-5-phenylpent-2-enoate

ethyl (4S,2E)-4-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-5-phenylpent-2-enoate