N⁶-benzoyl-9-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]adenine
• CAS No.: 323203-92-5
• Molecular Formula: C₂₂H₂₁N₅O₄
• Molecular Weight: 419.44

Synonyms:N⁶-benzoyl-9-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]adenine

Chemical Property of N⁶-benzoyl-9-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]adenine

Chemical Property:

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Technology Process of N⁶-benzoyl-9-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]adenine

There total 2 articles about N⁶-benzoyl-9-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]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:

N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-α-L-talo-hept-6-ynofuranosyl]adenine (244263-90-9) → N6-benzoyl-9-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]adenine (323203-92-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / CH₂Cl₂ / 17 h / 15 °C

2: 50.4 mg / AIBN; Bu₃SnH / toluene / 1 h / 80 °C

3: 100 percent / TBAF / tetrahydrofuran / 3 h / 25 °C

With 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/1522-2675(20001108)83:11<2975::AID-HLCA2975>3.0.CO;2-2

Reference yield:

N6-benzoyl-9-{6,7-dideoxy-5-O-[(imidazol-1-yl)thiocarbonyl]-2,3-O-isopropylidene-7-C-(trimethylsilyl)-α-L-talo-hept-6-ynofuranosyl}adenine → N6-benzoyl-9-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]adenine (323203-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 50.4 mg / AIBN; Bu₃SnH / toluene / 1 h / 80 °C

2: 100 percent / TBAF / tetrahydrofuran / 3 h / 25 °C

With 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; In tetrahydrofuran; toluene;

DOI:10.1002/1522-2675(20001108)83:11<2975::AID-HLCA2975>3.0.CO;2-2

Reference yield: 71.0%

N6-benzoyl-9-[5,6,7-trideoxy-2,3-O-isopropylidene-β-D-ribo-hept-6-ynofuranosyl]adenine (323203-92-5) + 8-iodo-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosine (323203-86-7) → 2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosine-8-yl-(8->7')-N6-benzoyl-9-(2,3-O-isopropylidene-5,6,7-trideoxy-β-D-ribo-hept-6-ynofuranosyl)adenine

Guidance literature:

With copper(l) iodide; P(fur)3; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In triethylamine; at 25 - 80 ℃; for 2h;

DOI:10.1002/1522-2675(20001108)83:11<2975::AID-HLCA2975>3.0.CO;2-2

upstream raw materials:

N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-α-L-talo-hept-6-ynofuranosyl]adenine

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