9-(3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N²-acetyl-6-O-diphenylcarbamoylguanine

Base Information

• Chemical Name: 9-(3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N²-acetyl-6-O-diphenylcarbamoylguanine
• CAS No.: 917239-35-1
• Molecular Formula: C₃₄H₂₉N₉O₈
• Molecular Weight: 691.66

Synonyms:9-(3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N²-acetyl-6-O-diphenylcarbamoylguanine

Chemical Property of 9-(3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N²-acetyl-6-O-diphenylcarbamoylguanine

Chemical Property:

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Technology Process of 9-(3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N²-acetyl-6-O-diphenylcarbamoylguanine

There total 1 articles about 9-(3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N²-acetyl-6-O-diphenylcarbamoylguanine 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: 74.0%

3-azido-1,2-bis-O-acetyl-5-O-benzoyl-3-deoxy-D-ribofuranose + N2-acetyl-O6-(diphenylcarbamoyl)guanine (112233-74-6) → 9-(3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N2-acetyl-6-O-diphenylcarbamoylguanine (917239-35-1)

Guidance literature:

3-azido-1,2-bis-O-acetyl-5-O-benzoyl-3-deoxy-D-ribofuranose; N₂-acetyl-O₆-(diphenylcarbamoyl)guanine; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 50 - 60 ℃; for 1h;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 65 - 70 ℃; for 4h;

DOI:10.1080/15257770500267170

Reference yield: 78.0%

9-(3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N2-acetyl-6-O-diphenylcarbamoylguanine (917239-35-1) → 9-(3'-azido-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N2-acetyl-guanine (917239-36-2)

Guidance literature:

With pyridine; hydrazine hydrate; acetic acid; at 20 ℃; for 24h;

DOI:10.1080/15257770500267170

Reference yield:

9-(3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N2-acetyl-6-O-diphenylcarbamoylguanine (917239-35-1) → N2-acetylguanine (19962-37-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / hydrazine hydrate; acetic acid; pyridine / 24 h / 20 °C

2: 81 percent / pyridine / CH₂Cl₂ / -40 °C

3: TBAF / tetrahydrofuran / 0.75 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; hydrazine hydrate; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1080/15257770500267170

upstream raw materials:

N₂-acetyl-O₆-(diphenylcarbamoyl)guanine

Downstream raw materials:

9-(3'-azido-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N²-acetyl-guanine

9-(3'-azido-2'-O-triflyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N²-acetyl-guanine

N²-acetylguanine

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