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

Base Information

• Chemical Name: 9-(3'-azido-2'-O-triflyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N²-acetyl-guanine
• CAS No.: 917239-37-3
• Molecular Formula: C₂₀H₁₇F₃N₈O₈S
• Molecular Weight: 586.465

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

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

Chemical Property:

Purity/Quality:

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

There total 4 articles about 9-(3'-azido-2'-O-triflyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N²-acetyl-guanine 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%

9-(3'-azido-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N2-acetyl-guanine (917239-36-2) + trifluoromethylsulfonic anhydride (358-23-6) → 9-(3'-azido-2'-O-triflyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N2-acetyl-guanine (917239-37-3)

Guidance literature:

With pyridine; In dichloromethane; at -40 ℃;

DOI:10.1080/15257770500267170

Reference yield:

3-azido-1,2-bis-O-acetyl-5-O-benzoyl-3-deoxy-D-ribofuranose → 9-(3'-azido-2'-O-triflyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N2-acetyl-guanine (917239-37-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / 50 - 60 °C

1.2: 74 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 4 h / 65 - 70 °C

2.1: 78 percent / hydrazine hydrate; acetic acid; pyridine / 24 h / 20 °C

3.1: 81 percent / pyridine / CH₂Cl₂ / -40 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; hydrazine hydrate; acetic acid; In dichloromethane; acetonitrile;

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) → 9-(3'-azido-2'-O-triflyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N2-acetyl-guanine (917239-37-3)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; hydrazine hydrate; acetic acid; In dichloromethane;

DOI:10.1080/15257770500267170

upstream raw materials:

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

trifluoromethylsulfonic anhydride

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

N₂-acetyl-O₆-(diphenylcarbamoyl)guanine

Downstream raw materials:

N²-acetylguanine

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