L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-, phenylmethyl ester

Base Information

• Chemical Name: L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-, phenylmethyl ester
• CAS No.: 92515-43-0
• Molecular Formula: C28H31NO5
• Molecular Weight: 461.558
• Mol file: 92515-43-0.mol

Synonyms:Nα-tert-butoxycarbonyl-O-benzyl-L-tyrosine benzyl ester;Boc-Tyr(Bzl)-OBzl;(S)-3-(4-benzyloxyphenyl)-2-(tert-butoxycarbonylamino)propionic acid benzyl ester;(S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid benzyl ester;

Chemical Property of L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-, phenylmethyl ester

Chemical Property:

• PSA: 73.86000
• LogP: 5.83570

Purity/Quality:

(S)-Benzyl3-(4-(benzyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-, phenylmethyl ester

There total 6 articles about L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-, phenylmethyl 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-tyrosine benzyl ester (52799-86-7) → (S)-3-(4-benzyloxyphenyl)-2-(tert-butoxycarbonylamino)propionic acid benzyl ester (92515-43-0)

Guidance literature:

With indium(III) chloride; at 30 - 35 ℃; for 1h;

DOI:10.1055/s-2006-942492

Reference yield: 87.0%

Boc-Tyr-OH (3978-80-1) + benzyl bromide (100-39-0) → (S)-3-(4-benzyloxyphenyl)-2-(tert-butoxycarbonylamino)propionic acid benzyl ester (92515-43-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 48h;

DOI:10.1016/S0957-4166(03)00482-8

Reference yield: 79.0%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3,54784-43-9) + benzyl alcohol (100-51-6,185532-71-2) → (S)-3-(4-benzyloxyphenyl)-2-(tert-butoxycarbonylamino)propionic acid benzyl ester (92515-43-0)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 14h; Ambient temperature;

DOI:10.1248/cpb.47.563

upstream raw materials:

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

benzyl alcohol

Boc-Tyr-OH

benzyl bromide

Downstream raw materials:

(4S)-4-(4-hydroxybenzyl)-1,3-oxazolidin-2-one

N^α-tert-butoxycarbonyl-L-prolyl-L-isoleucyl-glycyl-N^im-2,4-dinitrophenyl-L-histidyl-L-leucyl-O-benzyl-L-tyrosine benzyl ester

N^α-tert-butoxycarbonyl-L-isoleucyl-glycyl-N^im-2,4-dinitrophenyl-L-histidyl-L-leucyl-O-benzyl-L-tyrosine benzyl ester

L-isoleucyl-glycyl-N^im-2,4-dinitrophenyl-L-histidyl-L-leucyl-O-benzyl-L-tyrosine benzyl ester hydrochloride