N⁴-acetyl-1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-ethynylcytosine

Base Information

• Chemical Name: N⁴-acetyl-1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-ethynylcytosine
• CAS No.: 1472616-83-3
• Molecular Formula: C₃₄H₃₃N₃O₇
• Molecular Weight: 595.652

Synonyms:N⁴-acetyl-1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-ethynylcytosine

Chemical Property of N⁴-acetyl-1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-ethynylcytosine

Chemical Property:

Purity/Quality:

98%,99%, ^*data from raw suppliers

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Technology Process of N⁴-acetyl-1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-ethynylcytosine

There total 3 articles about N⁴-acetyl-1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-ethynylcytosine 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: 73.0%

1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-ethynylcytosine (1472616-82-2) + acetic anhydride (108-24-7) → N4-acetyl-1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-ethynylcytosine (1472616-83-3)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 36h;

DOI:10.1021/jo401780u

Reference yield:

4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-ethynylpyrimidin-2(1H)-one (69075-47-4) → N4-acetyl-1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-ethynylcytosine (1472616-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 5 h / 20 °C

2: N,N-dimethyl-formamide / 36 h / 20 °C

With pyridine; In N,N-dimethyl-formamide;

DOI:10.1021/jo401780u

Reference yield:

5-trimethylsilylethynyl-2′-deoxycytidine (1279719-43-5) → N4-acetyl-1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-ethynylcytosine (1472616-83-3)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / methanol / 1 h / 20 °C

2: pyridine / 5 h / 20 °C

3: N,N-dimethyl-formamide / 36 h / 20 °C

With pyridine; potassium carbonate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo401780u

upstream raw materials:

5-trimethylsilylethynyl-2′-deoxycytidine

1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-ethynylcytosine

acetic anhydride

4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-ethynylpyrimidin-2(1H)-one

Downstream raw materials:

N⁴-acetyl-1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-ethynylcytosine 3′-(2-cyanoethyl)-N,N-diisopropylphosphoramidite

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