(+/-)-9-[(1-trityloxyethyl)(3-di-tert-butylcarbonyloxymethylphosphonomethoxy)propyl]-N⁶-trityladenine

Base Information

• Chemical Name: (+/-)-9-[(1-trityloxyethyl)(3-di-tert-butylcarbonyloxymethylphosphonomethoxy)propyl]-N⁶-trityladenine
• CAS No.: 889886-14-0
• Molecular Formula: C₆₁H₆₆N₅O₉P
• Molecular Weight: 1044.2

Synonyms:(+/-)-9-[(1-trityloxyethyl)(3-di-tert-butylcarbonyloxymethylphosphonomethoxy)propyl]-N⁶-trityladenine

Chemical Property of (+/-)-9-[(1-trityloxyethyl)(3-di-tert-butylcarbonyloxymethylphosphonomethoxy)propyl]-N⁶-trityladenine

Chemical Property:

Purity/Quality:

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Technology Process of (+/-)-9-[(1-trityloxyethyl)(3-di-tert-butylcarbonyloxymethylphosphonomethoxy)propyl]-N⁶-trityladenine

There total 10 articles about (+/-)-9-[(1-trityloxyethyl)(3-di-tert-butylcarbonyloxymethylphosphonomethoxy)propyl]-N⁶-trityladenine 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: 52.0%

(+/-)-9-[(1-trityloxyethyl)(3-phosphonomethoxy)propyl]-N6-trityladenine (889886-13-9) + Chloromethyl pivalate (18997-19-8) → (+/-)-9-[(1-trityloxyethyl)(3-di-tert-butylcarbonyloxymethylphosphonomethoxy)propyl]-N6-trityladenine (889886-14-0)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 96h;

DOI:10.1080/15257770500265612

Reference yield:

(+/-)-5-O-pivaloylpentane-1,3,5-triol (889886-05-9) → (+/-)-9-[(1-trityloxyethyl)(3-di-tert-butylcarbonyloxymethylphosphonomethoxy)propyl]-N6-trityladenine (889886-14-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 13 g / imidazole / CH₂Cl₂ / 1 h / 20 °C

2.1: 70 percent / Ph₃P; diethyl azodicarboxylate / dioxane / 19 h / 20 °C

3.1: 65 percent / NaOMe / methanol / 17 h / 20 °C

4.1: 54 percent / DMAP; pyridine; Et₃N / 17 h / Heating

5.1: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

6.1: NaH / dimethylformamide / 18 h / 20 °C

6.2: 0.15 g / Et₃N; TMSI / dimethylformamide / 13 h / 20 °C

7.1: 52 percent / Et₃N / dimethylformamide / 96 h / 20 °C

With pyridine; 1H-imidazole; dmap; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Mitsunobu reaction;

DOI:10.1080/15257770500265612

Reference yield:

(+/-)-1-O-pivaloyl-3,5-O-isopropylidenepentane-1,3,5-triol (889886-04-8) → (+/-)-9-[(1-trityloxyethyl)(3-di-tert-butylcarbonyloxymethylphosphonomethoxy)propyl]-N6-trityladenine (889886-14-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: AcOH / H₂O / 15 h / 50 - 55 °C

2.1: 13 g / imidazole / CH₂Cl₂ / 1 h / 20 °C

3.1: 70 percent / Ph₃P; diethyl azodicarboxylate / dioxane / 19 h / 20 °C

4.1: 65 percent / NaOMe / methanol / 17 h / 20 °C

5.1: 54 percent / DMAP; pyridine; Et₃N / 17 h / Heating

6.1: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

7.1: NaH / dimethylformamide / 18 h / 20 °C

7.2: 0.15 g / Et₃N; TMSI / dimethylformamide / 13 h / 20 °C

8.1: 52 percent / Et₃N / dimethylformamide / 96 h / 20 °C

With pyridine; 1H-imidazole; dmap; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; acetic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 3.1: Mitsunobu reaction;

DOI:10.1080/15257770500265612

upstream raw materials:

(+/-)-9-[(1-trityloxyethyl)(3-phosphonomethoxy)propyl]-N⁶-trityladenine

Chloromethyl pivalate

(+/-)-5-O-pivaloylpentane-1,3,5-triol

(+/-)-1-O-pivaloyl-3,5-O-isopropylidenepentane-1,3,5-triol

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