N⁶-benzoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]adenosine

Base Information

• Chemical Name: N⁶-benzoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]adenosine
• CAS No.: 445433-96-5
• Molecular Formula: C₃₆H₄₇N₅O₇SSi₂
• Molecular Weight: 751.024

Synonyms:N⁶-benzoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]adenosine

Chemical Property of N⁶-benzoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]adenosine

Chemical Property:

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Technology Process of N⁶-benzoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]adenosine

There total 6 articles about N⁶-benzoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]adenosine 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: 68.0%

phenylcarbonochloridothioate (1005-56-7) + C28(13)CH43N5O6Si2 (445433-92-1) → N6-benzoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]adenosine (445433-96-5)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1021/jo016281q

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-[5-13C]ribose (54447-56-2) → N6-benzoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]adenosine (445433-96-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / trimethylsilyl trifluoromethanesulfonate / toluene / 80 °C

2: NaOH; pyridine / methanol; H₂O

3: 228 mg / pyridine

4: 68 percent / pyridine / 20 °C

With pyridine; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; In methanol; water; toluene;

DOI:10.1021/jo016281q

Reference yield:

methyl 2,3,5-tri-O-benzoyl-D-[5-13C]ribofuranoside (184000-83-7) → N6-benzoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]adenosine (445433-96-5)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂SO₄; AcOH / 3 h / 0 °C

2: 80 percent / trimethylsilyl trifluoromethanesulfonate / toluene / 80 °C

3: NaOH; pyridine / methanol; H₂O

4: 228 mg / pyridine

5: 68 percent / pyridine / 20 °C

With pyridine; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic acid; In methanol; water; toluene;

DOI:10.1021/jo016281q

upstream raw materials:

phenylcarbonochloridothioate

C₂₈⁽¹³⁾CH₄₃N₅O₆Si₂

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-[5-13C]ribose

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

Downstream raw materials:

N⁶-benzoyl-2'-deoxy-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]adenosine

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