methyl O-[trans-3-(benzyloxy)cyclobutyl]-N-(tert-butoxycarbonyl)-L-tyrosine

Base Information

• Chemical Name: methyl O-[trans-3-(benzyloxy)cyclobutyl]-N-(tert-butoxycarbonyl)-L-tyrosine
• CAS No.: 1262278-69-2
• Molecular Formula: C₂₆H₃₃NO₆
• Molecular Weight: 455.551
• Mol file: 1262278-69-2.mol

Synonyms:methyl O-[trans-3-(benzyloxy)cyclobutyl]-N-(tert-butoxycarbonyl)-L-tyrosine

Chemical Property of methyl O-[trans-3-(benzyloxy)cyclobutyl]-N-(tert-butoxycarbonyl)-L-tyrosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl O-[trans-3-(benzyloxy)cyclobutyl]-N-(tert-butoxycarbonyl)-L-tyrosine

There total 5 articles about methyl O-[trans-3-(benzyloxy)cyclobutyl]-N-(tert-butoxycarbonyl)-L-tyrosine 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: 88.0%

(±)-cis-(1s,3s)-3-(benzyloxy)cyclobutan-1-ol (233276-35-2) + (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester (4326-36-7) → methyl O-[trans-3-(benzyloxy)cyclobutyl]-N-(tert-butoxycarbonyl)-L-tyrosine (1262278-69-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In 1,2-dimethoxyethane; at 20 ℃; for 23h; Inert atmosphere;

DOI:10.1016/j.bmc.2012.11.049

Reference yield:

benzyl bromide (100-39-0) → methyl O-[trans-3-(benzyloxy)cyclobutyl]-N-(tert-butoxycarbonyl)-L-tyrosine (1262278-69-2)

Guidance literature:

Multi-step reaction with 5 steps

1: mercury(I) chloride / 160 °C

2: n-butyllithium / tetrahydrofuran

3: hydrogenchloride / tetrahydrofuran

4: sodium tetrahydroborate / ethanol / 3 h / 0 °C

5: diethylazodicarboxylate; triphenylphosphine / 1,2-dimethoxyethane / 23 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; mercury(I) chloride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; 5: |Mitsunobu Displacement;

DOI:10.1016/j.bmc.2012.11.049

Reference yield:

(2-bromo-1-bromomethylethoxymethyl)benzene (35995-55-2) → methyl O-[trans-3-(benzyloxy)cyclobutyl]-N-(tert-butoxycarbonyl)-L-tyrosine (1262278-69-2)

Guidance literature:

Multi-step reaction with 4 steps

1: n-butyllithium / tetrahydrofuran

2: hydrogenchloride / tetrahydrofuran

3: sodium tetrahydroborate / ethanol / 3 h / 0 °C

4: diethylazodicarboxylate; triphenylphosphine / 1,2-dimethoxyethane / 23 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; 4: |Mitsunobu Displacement;

DOI:10.1016/j.bmc.2012.11.049

upstream raw materials:

(±)-cis-(1s,3s)-3-(benzyloxy)cyclobutan-1-ol

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

3-benzyloxy cyclobutanone

benzyl bromide

Downstream raw materials:

methyl N-(tert-butoxycarbonyl)-O-(trans-3-hydroxycyclobutyl)-L-tyrosine

methyl N-(tert-butoxycarbonyl)-O-(cis-3-fluorocyclobutyl)-L-tyrosine

N-(tert-butoxycarbonyl)-O-(cis-3-fluorocyclobutyl)-L-tyrosine

O-(cis-3-fluorocyclobutyl)-L-tyrosine hydrochloride salt