benzyl (R)-β-(tert-butoxycarbonylamino)-δ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]pentanoate

Base Information

• Chemical Name: benzyl (R)-β-(tert-butoxycarbonylamino)-δ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]pentanoate
• CAS No.: 623944-48-9
• Molecular Formula: C₂₉H₃₄N₄O₇
• Molecular Weight: 550.612

Synonyms:benzyl (R)-β-(tert-butoxycarbonylamino)-δ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]pentanoate

Chemical Property of benzyl (R)-β-(tert-butoxycarbonylamino)-δ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]pentanoate

Chemical Property:

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Technology Process of benzyl (R)-β-(tert-butoxycarbonylamino)-δ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]pentanoate

There total 2 articles about benzyl (R)-β-(tert-butoxycarbonylamino)-δ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]pentanoate 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: 44.0%

N-benzyloxycarbonyl cytosine (149411-91-6) + benzyl (S)-β-(tertbutoxycarbonylamino)-δ-bromopentanoate (623944-43-4) → benzyl (R)-β-(tert-butoxycarbonylamino)-δ-[N4-(benzyloxycarbonyl)cytosin-1-yl]pentanoate (623944-48-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 264h;

DOI:10.1002/ejoc.200300269

Reference yield:

(R)-5-(benzyloxy)-3-((tert-butoxycarbonyl)amino)-5-oxo-pentanoic acid → benzyl (R)-β-(tert-butoxycarbonylamino)-δ-[N4-(benzyloxycarbonyl)cytosin-1-yl]pentanoate (623944-48-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / BH₃*THF / tetrahydrofuran / 5 h / -5 °C

2: 79 percent / CBr₄; PPh₃ / CH₂Cl₂ / 15 h / -20 - 20 °C

3: 44 percent / K₂CO₃; TBAI / dimethylformamide / 264 h / 20 °C

With borane-THF; carbon tetrabromide; tetra-(n-butyl)ammonium iodide; potassium carbonate; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200300269

Reference yield: 63.0%

benzyl (R)-β-(tert-butoxycarbonylamino)-δ-[N4-(benzyloxycarbonyl)cytosin-1-yl]pentanoate (623944-48-9) → (R)-β-(tert-butoxycarbonylamino)-δ-[N4-(benzyloxycarbonyl)cytosin-1-yl]pentanoic acid (623944-52-5)

Guidance literature:

With sodium hydroxide; water; In 1,4-dioxane; at 20 ℃; for 24h;

DOI:10.1002/ejoc.200300269

upstream raw materials:

N-benzyloxycarbonyl cytosine

benzyl (S)-β-(tertbutoxycarbonylamino)-δ-bromopentanoate

Downstream raw materials:

(R)-β-(tert-butoxycarbonylamino)-δ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]pentanoic acid

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