N⁶-benzoyl-2'-S-(4-methoxybenzyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-thioadenosine

Base Information

• Chemical Name: N⁶-benzoyl-2'-S-(4-methoxybenzyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-thioadenosine
• CAS No.: 875112-49-5
• Molecular Formula: C₃₇H₅₁N₅O₆SSi₂
• Molecular Weight: 750.079
• Mol file: 875112-49-5.mol

Synonyms:N⁶-benzoyl-2'-S-(4-methoxybenzyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-thioadenosine

Chemical Property of N⁶-benzoyl-2'-S-(4-methoxybenzyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-thioadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-benzoyl-2'-S-(4-methoxybenzyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-thioadenosine

There total 2 articles about N⁶-benzoyl-2'-S-(4-methoxybenzyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-thioadenosine 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: 91.0%

p-methoxybenzylmercaptan (6258-60-2) + 6-N-benzoyl-9-<3,5-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)-2-O-trifluoromethanesulfonyl-β-D-arabinofuranosyl>adenine (136923-03-0) → N6-benzoyl-2'-S-(4-methoxybenzyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-thioadenosine (875112-49-5)

Guidance literature:

p-methoxybenzylmercaptan; With sodium hydride; In dimethyl sulfoxide; at 25 ℃; for 0.166667h;

6-N-benzoyl-9-<3,5-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)-2-O-trifluoromethanesulfonyl-β-D-arabinofuranosyl>adenine; In dimethyl sulfoxide; at 10 ℃; for 0.166667h;

DOI:10.1002/hlca.200590233

Reference yield:

N6-benzoyl-3′,5′-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-adenosine-9-β-D-arabinofuranoside (79848-03-6) → N6-benzoyl-2'-S-(4-methoxybenzyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-thioadenosine (875112-49-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / CH₂Cl₂ / -15 - 10 °C

2.1: NaH / dimethylsulfoxide / 0.17 h / 25 °C

2.2: 91 percent / dimethylsulfoxide / 0.17 h / 10 °C

With pyridine; sodium hydride; In dichloromethane; dimethyl sulfoxide;

DOI:10.1002/hlca.200590233

Reference yield: 86.0%

N6-benzoyl-2'-S-(4-methoxybenzyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-thioadenosine (875112-49-5) + n-butylsulfenyl chloride (14925-97-4) → N6-benzoyl-2'-(butyldithio)-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine (875112-50-8)

Guidance literature:

With acetic acid; In dichloromethane; at 25 ℃; for 48h;

DOI:10.1002/hlca.200590233

upstream raw materials:

p-methoxybenzylmercaptan

6-N-benzoyl-9-<3,5-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)-2-O-trifluoromethanesulfonyl-β-D-arabinofuranosyl>adenine

N⁶-benzoyl-3′,5′-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-adenosine-9-β-D-arabinofuranoside

Downstream raw materials:

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

N⁶-benzoyl-2'-(butyldithio)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)adenosine