3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-N⁶-benzoyl-3-deazaadenosine

Base Information

• Chemical Name: 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-N⁶-benzoyl-3-deazaadenosine
• CAS No.: 886227-26-5
• Molecular Formula: C₃₀H₄₄N₄O₅Si₂
• Molecular Weight: 596.874

Synonyms:3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-N⁶-benzoyl-3-deazaadenosine

Chemical Property of 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-N⁶-benzoyl-3-deazaadenosine

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-N⁶-benzoyl-3-deazaadenosine

There total 12 articles about 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-N⁶-benzoyl-3-deazaadenosine 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:

3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-[(imidazol-1-yl)thiocarbonyl]-N6-benzoyl-3-deazaadenosine (886227-25-4) → 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-N6-benzoyl-3-deazaadenosine (886227-26-5)

Guidance literature:

With azobisisobutyronitrile; tri-n-butyl-tin hydride; In toluene; at 75 ℃; for 3h;

DOI:10.1021/ja0588454

Reference yield:

3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-3-deazaadenosine (886227-23-2) → 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-N6-benzoyl-3-deazaadenosine (886227-26-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: chlorotrimethylsilane; pyridine / 0.83 h / 0 °C

1.2: pyridine / 3.5 h / 0 - 20 °C

1.3: 93 percent / aq. NH₃ / 3 h / 20 °C

2.1: dimethylformamide / 4 h / 20 °C

3.1: 51 mg / α,α'-azo-isobutyronitrile; n-Bu3SnH / toluene / 3 h / 75 °C

With pyridine; chloro-trimethyl-silane; azobisisobutyronitrile; tri-n-butyl-tin hydride; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0588454

Reference yield:

5-iodo-1-[2',3',5'-O-tris(tert-butyldimethylsilyl)-β-D-ribofuranosyl]imidazole-4-carbonitrile (886227-20-9) → 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-N6-benzoyl-3-deazaadenosine (886227-26-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Pd(PhCN)2Cl₂; Et₃N / acetonitrile / 20 h / 110 °C

1.2: 50 percent / NH₃; methanol / 14 h / 120 °C

2.1: 79 percent / Amberlite IRA 900 fluoride-form / toluene / 6 h / Heating

3.1: 81 percent / pyridine / 5 h / 20 °C

4.1: chlorotrimethylsilane; pyridine / 0.83 h / 0 °C

4.2: pyridine / 3.5 h / 0 - 20 °C

4.3: 93 percent / aq. NH₃ / 3 h / 20 °C

5.1: dimethylformamide / 4 h / 20 °C

6.1: 51 mg / α,α'-azo-isobutyronitrile; n-Bu3SnH / toluene / 3 h / 75 °C

With pyridine; bis(benzonitrile)palladium(II) dichloride; chloro-trimethyl-silane; Amberlite IRA 900 fluoride-form; azobisisobutyronitrile; tri-n-butyl-tin hydride; triethylamine; In N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja0588454

upstream raw materials:

3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-[(imidazol-1-yl)thiocarbonyl]-N⁶-benzoyl-3-deazaadenosine

3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-3-deazaadenosine

5-iodo-1-[2',3',5'-O-tris(tert-butyldimethylsilyl)-β-D-ribofuranosyl]imidazole-4-carbonitrile

5-amino-1-[2',3',5'-O-tris(tert-butyldimethylsilyl)-β-D-ribofuranosyl]imidazole-4-carbonitrile

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-N⁶-benzoyl-3-deazaadenosine

2'-deoxy-3'-O-[(N,N-diisopropylamino)-(β-cyanoethoxy)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-3-deazaadenosine

2'-deoxy-N⁶-benzoyl-3-deazaadenosine

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