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

Base Information

• Chemical Name: N⁶-benzoyl-5'(S)-C-<methyl>-2',3'-O-isopropylidene-5'-O-(p-toluenesulfonyl)adenosine
• CAS No.: 107961-44-4
• Molecular Formula: C₃₃H₃₈N₆O₉S
• Molecular Weight: 694.766

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

Chemical Property of N⁶-benzoyl-5'(S)-C-<methyl>-2',3'-O-isopropylidene-5'-O-(p-toluenesulfonyl)adenosine

Chemical Property:

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Technology Process of N⁶-benzoyl-5'(S)-C-<methyl>-2',3'-O-isopropylidene-5'-O-(p-toluenesulfonyl)adenosine

There total 8 articles about N⁶-benzoyl-5'(S)-C-<methyl>-2',3'-O-isopropylidene-5'-O-(p-toluenesulfonyl)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: 75.0%

p-toluenesulfonyl chloride (98-59-9) + N6-benzoyl-5'(S)-C-<methyl>-2',3'-O-isopropylideneadenosine (107961-42-2) → N6-benzoyl-5'(S)-C-<methyl>-2',3'-O-isopropylidene-5'-O-(p-toluenesulfonyl)adenosine (107961-44-4)

Guidance literature:

With pyridine; at 20 ℃; for 28h;

DOI:10.1021/jm00388a024

Reference yield:

N6-benzoyl-5'(R)-C-(nitromethyl)-2',3'-O-isopropylideneadenosine (84757-69-7) → N6-benzoyl-5'(S)-C-<methyl>-2',3'-O-isopropylidene-5'-O-(p-toluenesulfonyl)adenosine (107961-44-4)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / PtO₂ / methanol / 16 h / 20 °C / 2585.7 Torr

2: CH₂Cl₂ / 1 h / 20 °C

3: 85 percent / pyridine / 28 h / 20 °C

4: 48 percent / KNO₂ / dimethylsulfoxide / 12 h / 85 - 90 °C

5: 75 percent / pyridine / 28 h / 20 °C

With pyridine; potassium nitrite; hydrogen; platinum(IV) oxide; In methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jm00388a024

Reference yield:

N6-benzoyl-5'(S)-C-(nitromethyl)-2',3'-O-isopropylideneadenosine (84757-76-6) → N6-benzoyl-5'(S)-C-<methyl>-2',3'-O-isopropylidene-5'-O-(p-toluenesulfonyl)adenosine (107961-44-4)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / PtO₂ / methanol / 16 h / 20 °C / 2585.7 Torr

2: CH₂Cl₂ / 1 h / 20 °C

3: 75 percent / pyridine / 28 h / 20 °C

With pyridine; hydrogen; platinum(IV) oxide; In methanol; dichloromethane;

DOI:10.1021/jm00388a024

upstream raw materials:

p-toluenesulfonyl chloride

N⁶-benzoyl-5'(S)-C-<methyl>-2',3'-O-isopropylideneadenosine

di-tert-butyl dicarbonate

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

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