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

Base Information

• Chemical Name: 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-[(imidazol-1-yl)thiocarbonyl]-N⁶-benzoyl-3-deazaadenosine
• CAS No.: 886227-25-4
• Molecular Formula: C₃₄H₄₆N₆O₆SSi₂
• Molecular Weight: 723.013

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-[(imidazol-1-yl)thiocarbonyl]-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)-3-deazaadenosine (886227-23-2) → 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-[(imidazol-1-yl)thiocarbonyl]-N6-benzoyl-3-deazaadenosine (886227-25-4)

Guidance literature:

Multi-step reaction with 2 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

With pyridine; chloro-trimethyl-silane; In N,N-dimethyl-formamide;

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'-O-[(imidazol-1-yl)thiocarbonyl]-N6-benzoyl-3-deazaadenosine (886227-25-4)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/ja0588454

Reference yield:

5-amino-1-[2',3',5'-O-tris(tert-butyldimethylsilyl)-β-D-ribofuranosyl]imidazole-4-carbonitrile (886227-19-6) → 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-[(imidazol-1-yl)thiocarbonyl]-N6-benzoyl-3-deazaadenosine (886227-25-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 60 percent / diiodomethane; isoamyl nitrite / 0.75 h / 100 °C

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

2.2: 50 percent / NH₃; methanol / 14 h / 120 °C

3.1: 79 percent / Amberlite IRA 900 fluoride-form / toluene / 6 h / Heating

4.1: 81 percent / pyridine / 5 h / 20 °C

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

5.2: pyridine / 3.5 h / 0 - 20 °C

5.3: 93 percent / aq. NH₃ / 3 h / 20 °C

6.1: dimethylformamide / 4 h / 20 °C

With pyridine; bis(benzonitrile)palladium(II) dichloride; chloro-trimethyl-silane; diiodomethane; Amberlite IRA 900 fluoride-form; triethylamine; isopentyl nitrite; 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)-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

2',3',5'-O-tris(tert-butyldimethylsilyl)-1-(2,4-dinitrophenyl)inosine

Downstream raw materials:

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

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

2'-deoxy-N⁶-benzoyl-3-deazaadenosine

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

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