N²,O^5'-ditrityl-2-amino-6-chloro-9-[2-deoxy-2-fluoro-3-O-(tetrahydro-2-pyranyl)-β-D-ribofuranosyl]purine

Base Information

• Chemical Name: N²,O^5'-ditrityl-2-amino-6-chloro-9-[2-deoxy-2-fluoro-3-O-(tetrahydro-2-pyranyl)-β-D-ribofuranosyl]purine
• CAS No.: 514830-08-1
• Molecular Formula: C₅₃H₄₇ClFN₅O₄
• Molecular Weight: 872.439

Synonyms:N²,O^5'-ditrityl-2-amino-6-chloro-9-[2-deoxy-2-fluoro-3-O-(tetrahydro-2-pyranyl)-β-D-ribofuranosyl]purine

Chemical Property of N²,O^5'-ditrityl-2-amino-6-chloro-9-[2-deoxy-2-fluoro-3-O-(tetrahydro-2-pyranyl)-β-D-ribofuranosyl]purine

Chemical Property:

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Technology Process of N²,O^5'-ditrityl-2-amino-6-chloro-9-[2-deoxy-2-fluoro-3-O-(tetrahydro-2-pyranyl)-β-D-ribofuranosyl]purine

There total 8 articles about N²,O^5'-ditrityl-2-amino-6-chloro-9-[2-deoxy-2-fluoro-3-O-(tetrahydro-2-pyranyl)-β-D-ribofuranosyl]purine 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: 60.0%

N2,O5'-ditrityl-2-amino-6-chloro-9-[3-O-(tetrahydro-2-pyranyl)-β-D-arabinofuranosyl]purine (1053641-60-3) → N2,O5'-ditrityl-2-amino-6-chloro-9-[2-deoxy-2-fluoro-3-O-(tetrahydro-2-pyranyl)-β-D-ribofuranosyl]purine (514830-08-1)

Guidance literature:

With 4,4'-diaminostilbene-2,2'-disulfonic acid; In pyridine; dichloromethane; at 50 ℃; for 6h;

DOI:10.1081/NCN-120016479

Reference yield:

2-Amino-6-chloropurine riboside (2004-07-1) → N2,O5'-ditrityl-2-amino-6-chloro-9-[2-deoxy-2-fluoro-3-O-(tetrahydro-2-pyranyl)-β-D-ribofuranosyl]purine (514830-08-1)

Guidance literature:

Multi-step reaction with 7 steps

1: imidazole / dimethylformamide

2: Et₃N; DMAP / CH₂Cl₂ / 0.17 h / 20 °C

3: 13.4 g / dimethylformamide / 10 h / 50 °C

4: 93 percent / TBAF; AcOH / tetrahydrofuran / 2 h / 20 °C

5: 69 percent / DMAP; Et₃N / dimethylformamide / 50 °C

6: 80 percent / p-TsOH / dimethylformamide / 4 °C

7: 60 percent / DAST / pyridine; CH₂Cl₂ / 6 h / 50 °C

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; acetic acid; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1081/NCN-120016479

Reference yield:

trityl chloride (76-83-5) → N2,O5'-ditrityl-2-amino-6-chloro-9-[2-deoxy-2-fluoro-3-O-(tetrahydro-2-pyranyl)-β-D-ribofuranosyl]purine (514830-08-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / DMAP; Et₃N / dimethylformamide / 50 °C

2: 80 percent / p-TsOH / dimethylformamide / 4 °C

3: 60 percent / DAST / pyridine; CH₂Cl₂ / 6 h / 50 °C

With dmap; toluene-4-sulfonic acid; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; In pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1081/NCN-120016479

upstream raw materials:

N²,O^5'-ditrityl-2-amino-6-chloro-9-[3-O-(tetrahydro-2-pyranyl)-β-D-arabinofuranosyl]purine

2-Amino-6-chloropurine riboside

trityl chloride

2-amino-6-chloro-9-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]purine

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