N⁶-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-8,2'-ethanoadenosine

Base Information

• Chemical Name: N⁶-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-8,2'-ethanoadenosine
• CAS No.: 100034-64-8
• Molecular Formula: C₃₁H₄₅N₅O₅Si₂
• Molecular Weight: 623.9

Synonyms:N⁶-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-8,2'-ethanoadenosine

Chemical Property of N⁶-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-8,2'-ethanoadenosine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-8,2'-ethanoadenosine

There total 9 articles about N⁶-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-8,2'-ethanoadenosine 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: 83.0%

N6-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-7,8-dihydro-8,2'-ethanoadenosine (100034-63-7) → N6-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-8,2'-ethanoadenosine (100034-64-8)

Guidance literature:

With palladium on activated charcoal; In toluene; for 55h; Heating;

DOI:10.1248/cpb.34.15

Reference yield:

3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine (69304-45-6) → N6-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-8,2'-ethanoadenosine (100034-64-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) DMSO, (COCl)2; 2.) Et₃N / 1.) CH₂Cl₂, -60 - -70 deg C; 30 min; 2.) CH₂Cl₂, THF, 30 min; 3.) r.t., 1.5 h

2: 74 percent / CH₂Cl₂ / 30 h / Ambient temperature

3: NaBH₄ / ethanol / 6 h

4: 1.) pyridine, 4 h, 0 deg C; 2.) 0 deg C, overnight

5: 37 percent / LiI / butan-2-one / 0.67 h / Heating

6: 27 percent / AIBN, n-Bu₃SnH / benzene / 2.17 h / Heating

7: 83 percent / 5 percent Pd-carbon / toluene / 55 h / Heating

With sodium tetrahydroborate; palladium on activated charcoal; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; dimethyl sulfoxide; triethylamine; lithium iodide; In ethanol; dichloromethane; toluene; butanone; benzene;

DOI:10.1248/cpb.34.15

Reference yield:

9-(3,5-O-(tetraisopropylsiloxanediyl)-β-D-erythro-pentofuran-2-ulosyl)adenine (90318-44-8) → N6-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-8,2'-ethanoadenosine (100034-64-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / CH₂Cl₂ / 30 h / Ambient temperature

2: NaBH₄ / ethanol / 6 h

3: 1.) pyridine, 4 h, 0 deg C; 2.) 0 deg C, overnight

4: 37 percent / LiI / butan-2-one / 0.67 h / Heating

5: 27 percent / AIBN, n-Bu₃SnH / benzene / 2.17 h / Heating

6: 83 percent / 5 percent Pd-carbon / toluene / 55 h / Heating

With sodium tetrahydroborate; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium iodide; In ethanol; dichloromethane; toluene; butanone; benzene;

DOI:10.1248/cpb.34.15

upstream raw materials:

N⁶-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-7,8-dihydro-8,2'-ethanoadenosine

3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine

benzoyl chloride

9-(3,5-O-(tetraisopropylsiloxanediyl)-β-D-erythro-pentofuran-2-ulosyl)adenine

Downstream raw materials:

N⁶-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-8,2'-ethenoadenosine

2'-deoxy-8,2'-ethanoadenosine

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