(tert-butoxycarbonyl)-L-valine-L-(benzyl)-meta-tyrosine carboxylic acid ethyl ester

Base Information

• Chemical Name: (tert-butoxycarbonyl)-L-valine-L-(benzyl)-meta-tyrosine carboxylic acid ethyl ester
• CAS No.: 247186-20-5
• Molecular Formula: C₂₈H₃₈N₂O₆
• Molecular Weight: 498.62
• Mol file: 247186-20-5.mol

Synonyms:(tert-butoxycarbonyl)-L-valine-L-(benzyl)-meta-tyrosine carboxylic acid ethyl ester

Chemical Property of (tert-butoxycarbonyl)-L-valine-L-(benzyl)-meta-tyrosine carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (tert-butoxycarbonyl)-L-valine-L-(benzyl)-meta-tyrosine carboxylic acid ethyl ester

There total 5 articles about (tert-butoxycarbonyl)-L-valine-L-(benzyl)-meta-tyrosine carboxylic acid ethyl ester 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: 70.0%

t-Boc-L-valine (13734-41-3) + (S)-2-Amino-3-(3-benzyloxy-phenyl)-propionic acid ethyl ester → (tert-butoxycarbonyl)-L-valine-L-(benzyl)-meta-tyrosine carboxylic acid ethyl ester (247186-20-5)

Guidance literature:

With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran;

DOI:10.1002/(SICI)1521-3773(19990816)38:16<2443::AID-ANIE2443>3.0.CO;2-B

Reference yield:

3-benzyloxybenzyl bromide (1700-31-8) → (tert-butoxycarbonyl)-L-valine-L-(benzyl)-meta-tyrosine carboxylic acid ethyl ester (247186-20-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

1.2: 62 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.1: 71 percent / aq. HCl / acetonitrile / 2 h / 20 °C

3.1: 8.85 g / tetrahydrofuran / -15 - 20 °C

With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1021/ja021327y

Reference yield:

(2S,5R)-2-(3-benzyloxybenzyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine (247186-19-2) → (tert-butoxycarbonyl)-L-valine-L-(benzyl)-meta-tyrosine carboxylic acid ethyl ester (247186-20-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / aq. HCl / acetonitrile / 2 h / 20 °C

2: 8.85 g / tetrahydrofuran / -15 - 20 °C

With hydrogenchloride; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ja021327y

upstream raw materials:

t-Boc-L-valine

C₁₅H₂₇NO₆

3-benzyloxybenzyl bromide

(2S,5R)-2-(3-benzyloxybenzyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine

Downstream raw materials:

(tert-butoxycarbonyl)-L-valine-L-(benzyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl ester

(tert-butoxycarbonyl)-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl ester

hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid hexa-3,5-dienyl ester

hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid 2,2,2-trichloroethyl ester