9-[2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-C-ethynyl-β-D-arabinofuranosyl]-N⁶-(phenoxyacetyl)adenine

Base Information

• Chemical Name: 9-[2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-C-ethynyl-β-D-arabinofuranosyl]-N⁶-(phenoxyacetyl)adenine
• CAS No.: 205500-36-3
• Molecular Formula: C₄₁H₃₇N₅O₇
• Molecular Weight: 711.774

Synonyms:9-[2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-C-ethynyl-β-D-arabinofuranosyl]-N⁶-(phenoxyacetyl)adenine

Chemical Property of 9-[2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-C-ethynyl-β-D-arabinofuranosyl]-N⁶-(phenoxyacetyl)adenine

Chemical Property:

Purity/Quality:

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Technology Process of 9-[2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-C-ethynyl-β-D-arabinofuranosyl]-N⁶-(phenoxyacetyl)adenine

There total 7 articles about 9-[2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-C-ethynyl-β-D-arabinofuranosyl]-N⁶-(phenoxyacetyl)adenine 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: 61.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 9-(2'-deoxy-2'-C-ethynyl-β-D-arabinofuranosyl)-N6-(phenoxyacetyl)adenine (205500-35-2) → 9-[2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-C-ethynyl-β-D-arabinofuranosyl]-N6-(phenoxyacetyl)adenine (205500-36-3)

Guidance literature:

With pyridine; for 3h; Ambient temperature;

DOI:10.1016/S0960-894X(98)00060-2

Reference yield:

1-(phenoxyacetyl)-1H-imidazole (110009-60-4) → 9-[2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-C-ethynyl-β-D-arabinofuranosyl]-N6-(phenoxyacetyl)adenine (205500-36-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethyloxonium tetrafluoroborate / CH₂Cl₂ / 3 h / 20 °C

1.2: 74 percent / CH₂Cl₂ / 19 h / 20 °C

2.1: 95 percent / Bu₄NF / tetrahydrofuran; acetic acid / 1 h / 20 °C

3.1: 61 percent / pyridine / 5 h / 20 °C

With tetrabutyl ammonium fluoride; triethyloxonium fluoroborate; In tetrahydrofuran; pyridine; dichloromethane; acetic acid;

DOI:10.1002/1522-2675(200201)85:1<224::AID-HLCA224>3.0.CO;2-L

Reference yield:

9-{2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}adenine (205500-33-0) → 9-[2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-C-ethynyl-β-D-arabinofuranosyl]-N6-(phenoxyacetyl)adenine (205500-36-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethyloxonium tetrafluoroborate / CH₂Cl₂ / 3 h / 20 °C

1.2: 74 percent / CH₂Cl₂ / 19 h / 20 °C

2.1: 95 percent / Bu₄NF / tetrahydrofuran; acetic acid / 1 h / 20 °C

3.1: 61 percent / pyridine / 5 h / 20 °C

With tetrabutyl ammonium fluoride; triethyloxonium fluoroborate; In tetrahydrofuran; pyridine; dichloromethane; acetic acid;

DOI:10.1002/1522-2675(200201)85:1<224::AID-HLCA224>3.0.CO;2-L

upstream raw materials:

4,4'-dimethoxytrityl chloride

9-(2'-deoxy-2'-C-ethynyl-β-D-arabinofuranosyl)-N⁶-(phenoxyacetyl)adenine

1-(phenoxyacetyl)-1H-imidazole

9-{2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}adenine

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