N-[5'-O-(4,4'-dimethoxytrityl)-3'-amino-3'-deoxythymidin-3'-yl]-O-(thymidin-5'-yl)-methanephosphonamidate

Base Information

• Chemical Name: N-[5'-O-(4,4'-dimethoxytrityl)-3'-amino-3'-deoxythymidin-3'-yl]-O-(thymidin-5'-yl)-methanephosphonamidate
• CAS No.: 211575-79-0
• Molecular Formula: C₄₂H₄₈N₅O₁₂P
• Molecular Weight: 845.843

Synonyms:N-[5'-O-(4,4'-dimethoxytrityl)-3'-amino-3'-deoxythymidin-3'-yl]-O-(thymidin-5'-yl)-methanephosphonamidate

Chemical Property of N-[5'-O-(4,4'-dimethoxytrityl)-3'-amino-3'-deoxythymidin-3'-yl]-O-(thymidin-5'-yl)-methanephosphonamidate

Chemical Property:

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Technology Process of N-[5'-O-(4,4'-dimethoxytrityl)-3'-amino-3'-deoxythymidin-3'-yl]-O-(thymidin-5'-yl)-methanephosphonamidate

There total 4 articles about N-[5'-O-(4,4'-dimethoxytrityl)-3'-amino-3'-deoxythymidin-3'-yl]-O-(thymidin-5'-yl)-methanephosphonamidate 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: 86.0%

N-[5'-O-(4,4'-dimethoxytrityl)-3'-amino-3'-deoxythymidin-3'-yl]-O-(3'-O-acetylthymidin-5'-yl)-methanephosphonamidate (211575-74-5) → N-[5'-O-(4,4'-dimethoxytrityl)-3'-amino-3'-deoxythymidin-3'-yl]-O-(thymidin-5'-yl)-methanephosphonamidate (211575-79-0)

Guidance literature:

With ammonium hydroxide; In ethanol; at 4 ℃; for 17h; Alkaline hydrolysis;

DOI:10.1021/ol0259084

Reference yield:

3'-amino-5'-(4,4'-dimethoxytrityl)-3'-deoxythymidine (143526-94-7,139063-29-9) → N-[5'-O-(4,4'-dimethoxytrityl)-3'-amino-3'-deoxythymidin-3'-yl]-O-(thymidin-5'-yl)-methanephosphonamidate (211575-79-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / 0.25 h / 0 °C

1.2: pyridine / 2 h / 20 °C

2.1: 86 percent / NH₄OH / ethanol / 17 h / 4 °C / Alkaline hydrolysis

With ammonium hydroxide; In pyridine; ethanol;

DOI:10.1021/ol0259084

Reference yield:

Acetic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-methylphosphinoyloxymethyl-tetrahydro-furan-3-yl ester (439113-14-1) → N-[5'-O-(4,4'-dimethoxytrityl)-3'-amino-3'-deoxythymidin-3'-yl]-O-(thymidin-5'-yl)-methanephosphonamidate (211575-79-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trimethylsilyl chloride; I₂; Et₃N / pyridine / 0.25 h

1.2: pyridine / 12 h

2.1: 86 percent / NH₄OH / ethanol / 17 h / 4 °C / Alkaline hydrolysis

With ammonium hydroxide; chloro-trimethyl-silane; iodine; triethylamine; In pyridine; ethanol;

DOI:10.1021/ol0259084

upstream raw materials:

N-[5'-O-(4,4'-dimethoxytrityl)-3'-amino-3'-deoxythymidin-3'-yl]-O-(3'-O-acetylthymidin-5'-yl)-methanephosphonamidate

Acetic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-methylphosphinoyloxymethyl-tetrahydro-furan-3-yl ester

C₁₉H₃₂N₃O₆P

3'-amino-5'-(4,4'-dimethoxytrityl)-3'-deoxythymidine

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