(R)-tert-butyl 2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionate

Base Information

• Chemical Name: (R)-tert-butyl 2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionate
• CAS No.: 728944-91-0
• Molecular Formula: C₂₂H₂₇NO₅
• Molecular Weight: 385.46
• Mol file: 728944-91-0.mol

Synonyms:(R)-tert-butyl 2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionate

Chemical Property of (R)-tert-butyl 2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-tert-butyl 2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionate

There total 2 articles about (R)-tert-butyl 2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionate 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: 64.0%

(R)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionic acid (65806-89-5) + tert-butyl alcohol (75-65-0) → (R)-tert-butyl 2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionate (728944-91-0)

Guidance literature:

(R)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionic acid; With 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 23 ℃; for 0.5h;

tert-butyl alcohol; With dmap; In toluene; at 23 ℃; for 3h;

DOI:10.1002/ejoc.200300814

Reference yield:

N-α-benzyloxycarbonyl-D-tyrosine (64205-12-5) → (R)-tert-butyl 2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionate (728944-91-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 91 percent / NaOH / ethanol; H₂O / 3 h / Heating

2.1: 2,4,6-Cl₃C₆H₂COCl; iPr₂NEt / tetrahydrofuran / 0.5 h / 23 °C

2.2: 64 percent / DMAP / toluene / 3 h / 23 °C

With sodium hydroxide; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; water;

DOI:10.1002/ejoc.200300814

Reference yield: 95.0%

(R)-tert-butyl 2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionate (728944-91-0) → (R)-tert-butyl 2-amino-3-(4-methoxyphenyl)propionate (281190-95-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 2h;

DOI:10.1002/ejoc.200300814

upstream raw materials:

(R)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionic acid

tert-butyl alcohol

N-α-benzyloxycarbonyl-D-tyrosine

Downstream raw materials:

(R)-tert-butyl 2-amino-3-(4-methoxyphenyl)propionate

Cryptophycin 4

desepoxyarenastatin A

cryptophycin-24