N⁶-benzoyl-5'(R)-C-(hydroxymethyl)-2',3'-O-isopropylidene-5'-O-(p-tolylsulfonyl)adenosine

Base Information

• Chemical Name: N⁶-benzoyl-5'(R)-C-(hydroxymethyl)-2',3'-O-isopropylidene-5'-O-(p-tolylsulfonyl)adenosine
• CAS No.: 109087-21-0
• Molecular Formula: C₂₈H₂₉N₅O₈S
• Molecular Weight: 595.633

Synonyms:N⁶-benzoyl-5'(R)-C-(hydroxymethyl)-2',3'-O-isopropylidene-5'-O-(p-tolylsulfonyl)adenosine

Chemical Property of N⁶-benzoyl-5'(R)-C-(hydroxymethyl)-2',3'-O-isopropylidene-5'-O-(p-tolylsulfonyl)adenosine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-benzoyl-5'(R)-C-(hydroxymethyl)-2',3'-O-isopropylidene-5'-O-(p-tolylsulfonyl)adenosine

There total 2 articles about N⁶-benzoyl-5'(R)-C-(hydroxymethyl)-2',3'-O-isopropylidene-5'-O-(p-tolylsulfonyl)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:

Toluene-4-sulfonic acid (R)-2-amino-1-[(3aR,4S,6R,6aR)-6-(6-benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-ethyl ester (109087-25-4) → N6-benzoyl-5'(R)-C-(hydroxymethyl)-2',3'-O-isopropylidene-5'-O-(p-tolylsulfonyl)adenosine (109087-21-0)

Guidance literature:

With acetic acid; sodium nitrite; In tetrahydrofuran; at 22 ℃; for 0.5h; Yield given;

DOI:10.1021/jm00392a013

Reference yield:

N6-benzoyl-5'(R)-C-<methyl>-2',3'-O-isopropylidene-5'-O-(p-toluenesulfonyl)adenosine (107961-45-5) → N6-benzoyl-5'(R)-C-(hydroxymethyl)-2',3'-O-isopropylidene-5'-O-(p-tolylsulfonyl)adenosine (109087-21-0)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / 0.08 h / 4 °C

2: aq. AcOH, NaNO₂ / tetrahydrofuran / 0.5 h / 22 °C

With acetic acid; trifluoroacetic acid; sodium nitrite; In tetrahydrofuran;

DOI:10.1021/jm00392a013

Reference yield:

N6-benzoyl-5'(R)-C-(hydroxymethyl)-2',3'-O-isopropylidene-5'-O-(p-tolylsulfonyl)adenosine (109087-21-0) → (S)-4-[(S)-2-[(3aR,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-(benzyloxy-hydroxy-phosphoryloxy)-ethylsulfanyl]-2-tert-butoxycarbonylamino-butyric acid methyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 2.) MeOH / 1.) EtOH, 1 h, 2.) EtOH, 22 deg C, 18 h

2: Et₃N / dimethylformamide / 1 h / 22 °C

3: methanol

4: pyridine, dicyclohexylcarbodiimide / 48 h / 22 °C

With pyridine; methanol; triethylamine; dicyclohexyl-carbodiimide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00392a013

upstream raw materials:

Toluene-4-sulfonic acid (R)-2-amino-1-[(3aR,4S,6R,6aR)-6-(6-benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-ethyl ester

N⁶-benzoyl-5'(R)-C-<methyl>-2',3'-O-isopropylidene-5'-O-(p-toluenesulfonyl)adenosine

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