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

Base Information

• Chemical Name: N⁶-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-7,8-dihydro-8,2'-ethanoadenosine
• CAS No.: 100034-63-7
• Molecular Formula: C₃₁H₄₇N₅O₅Si₂
• Molecular Weight: 625.916

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

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

There total 8 articles about N⁶-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-7,8-dihydro-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: 27.0%

N6,N6-dibenzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-(S)-(2-iodoethyl)adenosine (100034-59-1) → N6-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-7,8-dihydro-8,2'-ethanoadenosine (100034-63-7) + N6,N6-dibenzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-8,2'-ethanoadenosine (100034-60-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 2.16667h; Yields of byproduct given; 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-7,8-dihydro-8,2'-ethanoadenosine (100034-63-7)

Guidance literature:

Multi-step reaction with 6 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

With sodium tetrahydroborate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; dimethyl sulfoxide; triethylamine; lithium iodide; In ethanol; dichloromethane; 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-7,8-dihydro-8,2'-ethanoadenosine (100034-63-7)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1248/cpb.34.15

upstream raw materials:

N⁶,N⁶-dibenzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-(S)-(2-iodoethyl)adenosine

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

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

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