9-(5-O-(N-Phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-2-N-isobutyrylguanine

Base Information

• Chemical Name: 9-(5-O-(N-Phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-2-N-isobutyrylguanine
• CAS No.: 166758-20-9
• Molecular Formula: C₃₅H₃₁N₇O₈
• Molecular Weight: 677.673

Synonyms:9-(5-O-(N-Phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-2-N-isobutyrylguanine

Chemical Property of 9-(5-O-(N-Phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-2-N-isobutyrylguanine

Chemical Property:

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Technology Process of 9-(5-O-(N-Phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-2-N-isobutyrylguanine

There total 4 articles about 9-(5-O-(N-Phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-2-N-isobutyrylguanine 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: 69.0%

N-hydroxyphthalimide (524-38-9) + 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-2-N-isobutyrylguanine (161388-91-6) → 9-(5-O-(N-Phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-2-N-isobutyrylguanine (166758-20-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide; for 18h; Ambient temperature;

DOI:10.1021/jo00121a037

Reference yield:

diphenylcarbamic chloride (83-01-2) → 9-(5-O-(N-Phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-2-N-isobutyrylguanine (166758-20-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N, pyridine / 16 h / 4 °C

2: 69 percent / Ph₃P, DEAD / dimethylformamide; tetrahydrofuran / 18 h / Ambient temperature

With pyridine; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo00121a037

Reference yield:

N-[6-Hydroxy-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-isobutyramide (68892-42-2) → 9-(5-O-(N-Phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-2-N-isobutyrylguanine (166758-20-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N, pyridine / 16 h / 4 °C

2: 69 percent / Ph₃P, DEAD / dimethylformamide; tetrahydrofuran / 18 h / Ambient temperature

With pyridine; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo00121a037

upstream raw materials:

N-hydroxyphthalimide

9-(2-Deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-2-N-isobutyrylguanine

diphenylcarbamic chloride

N-[6-Hydroxy-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-isobutyramide

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