Nα-tert-butyloxycarbonyl-β-N4-benzyloxycarbonyl-cytosin-1-yl-alanine

Base Information

• Chemical Name: Nα-tert-butyloxycarbonyl-β-N4-benzyloxycarbonyl-cytosin-1-yl-alanine
• CAS No.: 197011-58-8
• Molecular Formula: C₂₀H₂₄N₄O₇
• Molecular Weight: 432.433
• Mol file: 197011-58-8.mol

Synonyms:Nα-tert-butyloxycarbonyl-β-N4-benzyloxycarbonyl-cytosin-1-yl-alanine

Chemical Property of Nα-tert-butyloxycarbonyl-β-N4-benzyloxycarbonyl-cytosin-1-yl-alanine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Nα-tert-butyloxycarbonyl-β-N4-benzyloxycarbonyl-cytosin-1-yl-alanine

There total 3 articles about Nα-tert-butyloxycarbonyl-β-N4-benzyloxycarbonyl-cytosin-1-yl-alanine 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: 85.0%

(S)-3-(tert-butoxycarbonylamino)-oxetan-2-one (98541-64-1) + N-benzyloxycarbonyl cytosine (149411-91-6) → Nα-tert-butyloxycarbonyl-β-N4-benzyloxycarbonyl-cytosin-1-yl-alanine (197011-58-8)

Guidance literature:

(S)-3-(tert-butoxycarbonylamino)-oxetan-2-one; N-benzyloxycarbonyl cytosine; With 1,8-diazabicyclo[5.4.0]undec-7-ene;

With acetic acid;

DOI:10.1002/anie.201805752

Reference yield:

(S)-N-(tert-butoxycarbonyl)serine (3262-72-4) → Nα-tert-butyloxycarbonyl-β-N4-benzyloxycarbonyl-cytosin-1-yl-alanine (197011-58-8)

Guidance literature:

Multi-step reaction with 2 steps

1: PPh₃; DEAD

2: 60 percent / DBU / dimethylsulfoxide / 3 h / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; diethylazodicarboxylate; In dimethyl sulfoxide;

DOI:10.1039/b411545g

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → Nα-tert-butyloxycarbonyl-β-N4-benzyloxycarbonyl-cytosin-1-yl-alanine (197011-58-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C

1.2: 14 h / 20 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethyl sulfoxide / 0.25 h

2.2: 2 h / 20 °C / Inert atmosphere

With sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.bmc.2016.07.008

upstream raw materials:

(S)-3-(tert-butoxycarbonylamino)-oxetan-2-one

N-benzyloxycarbonyl cytosine

(S)-N-(tert-butoxycarbonyl)serine

benzyl chloroformate