N²-acetyl-6-O-diphenylcarbamoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]guanosine

Base Information

• Chemical Name: N²-acetyl-6-O-diphenylcarbamoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]guanosine
• CAS No.: 445433-97-6
• Molecular Formula: C₄₄H₅₄N₆O₉SSi₂
• Molecular Weight: 900.174

Synonyms:N²-acetyl-6-O-diphenylcarbamoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]guanosine

Chemical Property of N²-acetyl-6-O-diphenylcarbamoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]guanosine

Chemical Property:

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Technology Process of N²-acetyl-6-O-diphenylcarbamoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]guanosine

There total 6 articles about N²-acetyl-6-O-diphenylcarbamoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]guanosine 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) + N2-acetyl-6-O-diphenylcarbamoyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5-13C]guanosine (445433-93-2) → N2-acetyl-6-O-diphenylcarbamoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]guanosine (445433-97-6)

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) → N2-acetyl-6-O-diphenylcarbamoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]guanosine (445433-97-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / trimethylsilyl trifluoromethanesulfonate / toluene / 80 °C

2: NaOH; pyridine / methanol; H₂O

3: 171 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) → N2-acetyl-6-O-diphenylcarbamoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]guanosine (445433-97-6)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂SO₄; AcOH / 3 h / 0 °C

2: 79 percent / trimethylsilyl trifluoromethanesulfonate / toluene / 80 °C

3: NaOH; pyridine / methanol; H₂O

4: 171 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

N²-acetyl-6-O-diphenylcarbamoyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5-13C]guanosine

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:

N²-acetyl-2'-deoxy-6-O-diphenylcarbamoyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]guanosine

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