[1-(4-tert-butoxy-benzyl)-3-diazo-2-oxo-propyl]-carbamic acid tert-butylester

Base Information

• Chemical Name: [1-(4-tert-butoxy-benzyl)-3-diazo-2-oxo-propyl]-carbamic acid tert-butylester
• CAS No.: 565430-72-0
• Molecular Formula: C₁₉H₂₇N₃O₄
• Molecular Weight: 361.441
• Mol file: 565430-72-0.mol

Synonyms:[1-(4-tert-butoxy-benzyl)-3-diazo-2-oxo-propyl]-carbamic acid tert-butylester

Chemical Property of [1-(4-tert-butoxy-benzyl)-3-diazo-2-oxo-propyl]-carbamic acid tert-butylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [1-(4-tert-butoxy-benzyl)-3-diazo-2-oxo-propyl]-carbamic acid tert-butylester

There total 2 articles about [1-(4-tert-butoxy-benzyl)-3-diazo-2-oxo-propyl]-carbamic acid tert-butylester 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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + Boc-D-Tyr(t-Bu)-OH (507276-74-6) → [1-(4-tert-butoxy-benzyl)-3-diazo-2-oxo-propyl]-carbamic acid tert-butylester (565430-72-0)

Guidance literature:

Boc-D-Tyr(t-Bu)-OH; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -20 ℃; for 0.333333h;

diazomethane; In tetrahydrofuran; diethyl ether; at -20 ℃; for 0.5h; Further stages.;

DOI:10.1021/ol027237f

Reference yield:

→ [1-(4-tert-butoxy-benzyl)-3-diazo-2-oxo-propyl]-carbamic acid tert-butylester (565430-72-0)

Guidance literature:

Reference yield:

[1-(4-tert-butoxy-benzyl)-3-diazo-2-oxo-propyl]-carbamic acid tert-butylester (565430-72-0) → 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enoic acid

Guidance literature:

Multi-step reaction with 5 steps

1: PhCO₂Ag; NEt₃ / 1.25 h

2: DIBAL-H / toluene / 1 h / -78 °C

3: tetrahydrofuran / 1.5 h / -78 - -40 °C

4: 81 percent / Cl₂(PCy)3(IMesH₂)RuCHPh / CH₂Cl₂ / 4 h / Heating

5: 70 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 3 h / 20 °C

With lithium hydroxide; dihydrogen peroxide; silver benzoate; diisobutylaluminium hydride; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1021/ol027237f

upstream raw materials:

diazomethane

Boc-D-Tyr(t-Bu)-OH