4-N-benzoyl-1-[3-C-ethynyl-2,3-O-isopropylidene-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine

Base Information

• Chemical Name: 4-N-benzoyl-1-[3-C-ethynyl-2,3-O-isopropylidene-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine
• CAS No.: 616239-76-0
• Molecular Formula: C₂₈H₂₅N₃O₇
• Molecular Weight: 515.522

Synonyms:4-N-benzoyl-1-[3-C-ethynyl-2,3-O-isopropylidene-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine

Chemical Property of 4-N-benzoyl-1-[3-C-ethynyl-2,3-O-isopropylidene-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine

Chemical Property:

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Technology Process of 4-N-benzoyl-1-[3-C-ethynyl-2,3-O-isopropylidene-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine

There total 2 articles about 4-N-benzoyl-1-[3-C-ethynyl-2,3-O-isopropylidene-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine 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:

benzoyl chloride (98-88-4) + 1-[3-C-ethynyl-2,3-O-isopropylidene-β-D-ribo-pentofuranosyl]cytosine perchlorate → 4-N-benzoyl-1-[3-C-ethynyl-2,3-O-isopropylidene-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine (616239-76-0)

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 20 ℃; for 5h;

DOI:10.1016/S0968-0896(03)00104-4

Reference yield:

3'-ethynylcytidine (180300-43-0) → 4-N-benzoyl-1-[3-C-ethynyl-2,3-O-isopropylidene-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine (616239-76-0)

Guidance literature:

Multi-step reaction with 2 steps

1: HClO₄ / acetone / 0.67 h / 20 °C

2: 6.5 g / Et₃N; DMAP / acetonitrile / 5 h / 20 °C

With dmap; perchloric acid; triethylamine; In acetone; acetonitrile;

DOI:10.1016/S0968-0896(03)00104-4

Reference yield: 85.0%

4-N-benzoyl-1-[3-C-ethynyl-2,3-O-isopropylidene-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine (616239-76-0) → 4-N-benzoyl-1-[3-C-ethynyl-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine (616239-77-1)

Guidance literature:

With trifluoroacetic acid; In water; at 20 ℃; for 1h;

DOI:10.1016/S0968-0896(03)00104-4

upstream raw materials:

benzoyl chloride

3'-ethynylcytidine

Downstream raw materials:

4-N-benzoyl-1-[3-C-ethynyl-5-O-benzoyl-β-D-ribo-pentofuranosyl]cytosine

1-[3-C-ethynyl-2,3-O-(3-nitrobenzylidene)-β-D-ribo-pentofuranosyl]cytosine

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