1-(5-O-benzyloxycarbonyl-3-aza-(N-tert-butoxycarbonyl)-pentyl)-N³-benzoyl thymine

Base Information

• Chemical Name: 1-(5-O-benzyloxycarbonyl-3-aza-(N-tert-butoxycarbonyl)-pentyl)-N³-benzoyl thymine
• CAS No.: 201735-87-7
• Molecular Formula: C₂₉H₃₃N₃O₈
• Molecular Weight: 551.596

Synonyms:1-(5-O-benzyloxycarbonyl-3-aza-(N-tert-butoxycarbonyl)-pentyl)-N³-benzoyl thymine

Chemical Property of 1-(5-O-benzyloxycarbonyl-3-aza-(N-tert-butoxycarbonyl)-pentyl)-N³-benzoyl thymine

Chemical Property:

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Technology Process of 1-(5-O-benzyloxycarbonyl-3-aza-(N-tert-butoxycarbonyl)-pentyl)-N³-benzoyl thymine

There total 4 articles about 1-(5-O-benzyloxycarbonyl-3-aza-(N-tert-butoxycarbonyl)-pentyl)-N³-benzoyl thymine 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: 81.0%

N-3-benzoylthymine (4330-20-5) + O-benzyloxycarbonyl-N-tert-butoxycarbonyl diethanolamine (201735-86-6) → 1-(5-O-benzyloxycarbonyl-3-aza-(N-tert-butoxycarbonyl)-pentyl)-N3-benzoyl thymine (201735-87-7)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 2.5h; Ambient temperature;

DOI:10.1080/15257779908043070

Reference yield:

N,N-bis(2-hydroxyethyl)-O-tert-butylcarbamate (103898-11-9) → 1-(5-O-benzyloxycarbonyl-3-aza-(N-tert-butoxycarbonyl)-pentyl)-N3-benzoyl thymine (201735-87-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / DMAP; Et₃N / CH₂Cl₂ / 18 h / 20 °C

2: 65 percent / Ph₃P; diethylazodicarboxylate / tetrahydrofuran / 2.5 h / 20 °C

With dmap; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 2: Mitsunobu reaction;

DOI:10.1081/NCN-120003176

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 1-(5-O-benzyloxycarbonyl-3-aza-(N-tert-butoxycarbonyl)-pentyl)-N3-benzoyl thymine (201735-87-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / tetrahydrofuran / 24 h / 20 °C

2: 54 percent / DMAP; Et₃N / CH₂Cl₂ / 18 h / 20 °C

3: 65 percent / Ph₃P; diethylazodicarboxylate / tetrahydrofuran / 2.5 h / 20 °C

With dmap; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 3: Mitsunobu reaction;

DOI:10.1081/NCN-120003176

upstream raw materials:

N-3-benzoylthymine

O-benzyloxycarbonyl-N-tert-butoxycarbonyl diethanolamine

di-tert-butyl dicarbonate

N,N-bis(2-hydroxyethyl)-O-tert-butylcarbamate

Downstream raw materials:

Carbonic acid 2-[[2-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-ethyl]-(5-{[2-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-ethyl]-tert-butoxycarbonyl-amino}-pentanoyl)-amino]-ethyl ester benzyl ester

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