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

Base Information

• Chemical Name: 5'-O-[(tert-butyl)(dimethyl)silyl]-3'-O-{[(2,2-dimethylpropanoyl)oxy]methyl}-N₆-[(4-methoxyphenyl)(diphenyl)methyl]adenosine
• CAS No.: 1166393-95-8
• Molecular Formula: C₄₂H₅₃N₅O₇Si
• Molecular Weight: 767.998

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

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

Chemical Property:

Purity/Quality:

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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]adenosine

There total 10 articles about 5'-O-[(tert-butyl)(dimethyl)silyl]-3'-O-{[(2,2-dimethylpropanoyl)oxy]methyl}-N₆-[(4-methoxyphenyl)(diphenyl)methyl]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: 92.0%

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) → 5'-O-[(tert-butyl)(dimethyl)silyl]-3'-O-{[(2,2-dimethylpropanoyl)oxy]methyl}-N6-[(4-methoxyphenyl)(diphenyl)methyl]adenosine (1166393-95-8)

Guidance literature:

With pyridine; hydrazine hydrate; acetic acid; at 20 ℃; for 6.5h; Cooling with ice;

DOI:10.1002/cbdv.201000288

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]adenosine (1166393-95-8)

Guidance literature:

Multi-step reaction with 6 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

6.1: pyridine; hydrazine hydrate; acetic acid / 6.5 h / 20 °C / Cooling with ice

With pyridine; dmap; water; sodium hydride; hydrazine hydrate; 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]adenosine (1166393-95-8)

Guidance literature:

Multi-step reaction with 7 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

7.1: pyridine; hydrazine hydrate; acetic acid / 6.5 h / 20 °C / Cooling with ice

With pyridine; dmap; water; sodium hydride; hydrazine hydrate; acetic acid; 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

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

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

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