5'-O-[(tert-butyl)(dimethyl)silyl]-3'-O-{[(2,2-dimethylpropanoyl)oxy]methyl}-N₆-[(4-methoxyphenyl)(diphenyl)methyl]-2'-O-(4-oxopentanoyl)adenosine

Base Information

• Chemical Name: 5'-O-[(tert-butyl)(dimethyl)silyl]-3'-O-{[(2,2-dimethylpropanoyl)oxy]methyl}-N₆-[(4-methoxyphenyl)(diphenyl)methyl]-2'-O-(4-oxopentanoyl)adenosine
• CAS No.: 1259402-50-0
• Molecular Formula: C₄₇H₅₉N₅O₉Si
• Molecular Weight: 866.099

Synonyms:5'-O-[(tert-butyl)(dimethyl)silyl]-3'-O-{[(2,2-dimethylpropanoyl)oxy]methyl}-N₆-[(4-methoxyphenyl)(diphenyl)methyl]-2'-O-(4-oxopentanoyl)adenosine

Chemical Property of 5'-O-[(tert-butyl)(dimethyl)silyl]-3'-O-{[(2,2-dimethylpropanoyl)oxy]methyl}-N₆-[(4-methoxyphenyl)(diphenyl)methyl]-2'-O-(4-oxopentanoyl)adenosine

Chemical Property:

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Technology Process of 5'-O-[(tert-butyl)(dimethyl)silyl]-3'-O-{[(2,2-dimethylpropanoyl)oxy]methyl}-N₆-[(4-methoxyphenyl)(diphenyl)methyl]-2'-O-(4-oxopentanoyl)adenosine

There total 11 articles about 5'-O-[(tert-butyl)(dimethyl)silyl]-3'-O-{[(2,2-dimethylpropanoyl)oxy]methyl}-N₆-[(4-methoxyphenyl)(diphenyl)methyl]-2'-O-(4-oxopentanoyl)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:

5'-O-(4-methoxyphenyl)diphenylmethyl-N6-(4-methoxyphenyl)diphenylmethyl-adenosine (110142-94-4) → 5'-O-[(tert-butyl)(dimethyl)silyl]-3'-O-{[(2,2-dimethylpropanoyl)oxy]methyl}-N6-[(4-methoxyphenyl)(diphenyl)methyl]-2'-O-(4-oxopentanoyl)adenosine (1259402-50-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C

1.2: 5 h

2.1: pyridine; dmap / 20 °C

3.1: water; acetic acid / 5 h / 40 °C

4.1: pyridine / 20 °C

5.1: pyridine / 40 °C

With pyridine; dmap; water; sodium hydride; acetic acid; In tetrahydrofuran;

DOI:10.1002/cbdv.201000288

Reference yield:

adenosine (58-61-7) → 5'-O-[(tert-butyl)(dimethyl)silyl]-3'-O-{[(2,2-dimethylpropanoyl)oxy]methyl}-N6-[(4-methoxyphenyl)(diphenyl)methyl]-2'-O-(4-oxopentanoyl)adenosine (1259402-50-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / 35 °C

2.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C

2.2: 5 h

3.1: pyridine; dmap / 20 °C

4.1: water; acetic acid / 5 h / 40 °C

5.1: pyridine / 20 °C

6.1: pyridine / 40 °C

With pyridine; dmap; water; sodium hydride; acetic acid; In tetrahydrofuran;

DOI:10.1002/cbdv.201000288

Reference yield:

3'-O-(acetyloxymethyl)adenosin-2'-yl adenosin-5'-yl 3-(acetyloxy)-2,2-bis(ethoxycarbonyl)propyl phosphate (1259402-79-3) → 5'-O-[(tert-butyl)(dimethyl)silyl]-3'-O-{[(2,2-dimethylpropanoyl)oxy]methyl}-N6-[(4-methoxyphenyl)(diphenyl)methyl]-2'-O-(4-oxopentanoyl)adenosine (1259402-50-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: hog liver carboxyesterase; water; sodium chloride / 37 °C / pH 7.5 / HEPES buffer; Enzymatic reaction

2.1: pyridine / 35 °C

3.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C

3.2: 5 h

4.1: pyridine; dmap / 20 °C

5.1: water; acetic acid / 5 h / 40 °C

6.1: pyridine / 20 °C

7.1: pyridine / 40 °C

With pyridine; dmap; hog liver carboxyesterase; water; sodium hydride; acetic acid; sodium chloride; In tetrahydrofuran;

DOI:10.1002/cbdv.201000288

upstream raw materials:

3'-O-{[(2,2-dimethylpropanoyl)-oxy]methyl}-N-[(4-methoxyphenyl)(diphenyl)methyl]-5'-O-[(4-methoxyphenyl)(diphenyl)methyl]adenosine

C₂₇H₄₃N₅O₈Si

mono-4-methoxytrityl chloride

3'-O-(acetyloxymethyl)adenosin-2'-yl adenosin-5'-yl 3-(acetyloxy)-2,2-bis(ethoxycarbonyl)propyl phosphate

Downstream raw materials:

2'-O-[bis(diethylamino)phosphanyl]-5'-O-[(tert-butyl)(dimethyl)silyl]-3'-O-{[(2,2-dimethylpropanoyl)oxy]methyl}-N₆-[(4-methoxyphenyl)(diphenyl)methyl]adenosine

5'-O-[(tert-butyl)(dimethyl)silyl]-3'-O-{[(2,2-dimethylpropanoyl)oxy]methyl}-N₆-[(4-methoxyphenyl)(diphenyl)methyl]adenosine

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