(+/-)-9-[(1-(4-monomethoxytrityloxy)methyl)(3-tert-butylcarbonyloxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine

Base Information

• Chemical Name: (+/-)-9-[(1-(4-monomethoxytrityloxy)methyl)(3-tert-butylcarbonyloxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine
• CAS No.: 889885-17-0
• Molecular Formula: C₅₄H₅₃N₅O₅
• Molecular Weight: 852.045

Synonyms:(+/-)-9-[(1-(4-monomethoxytrityloxy)methyl)(3-tert-butylcarbonyloxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine

Chemical Property of (+/-)-9-[(1-(4-monomethoxytrityloxy)methyl)(3-tert-butylcarbonyloxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine

Chemical Property:

Purity/Quality:

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Technology Process of (+/-)-9-[(1-(4-monomethoxytrityloxy)methyl)(3-tert-butylcarbonyloxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine

There total 5 articles about (+/-)-9-[(1-(4-monomethoxytrityloxy)methyl)(3-tert-butylcarbonyloxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine 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: 98.0%

(+/-)-9-[(1-hydroxymethyl)(3-tert-butylcarbonyloxy)propyl]adenine (889885-16-9) + mono-4-methoxytrityl chloride (14470-28-1) → (+/-)-9-[(1-(4-monomethoxytrityloxy)methyl)(3-tert-butylcarbonyloxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-17-0)

Guidance literature:

With pyridine; at 70 ℃; for 20h;

DOI:10.1080/15257770500268673

Reference yield:

(+/-)-4-O-pivaloylbutane-1,2,4-triol (889885-14-7) → (+/-)-9-[(1-(4-monomethoxytrityloxy)methyl)(3-tert-butylcarbonyloxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-17-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / imidazole / CH₂Cl₂ / 3 h / 20 °C

2: 69 percent / Ph₃P; diisopropy azodicarboxylate / dioxane / 16 h / 20 °C

3: 21.1 g / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

4: 98 percent / pyridine / 20 h / 70 °C

With pyridine; 1H-imidazole; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 2: Mitsunobu reaction;

DOI:10.1080/15257770500268673

Reference yield:

2,2-dimethyl-propionic acid 2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester (889885-13-6) → (+/-)-9-[(1-(4-monomethoxytrityloxy)methyl)(3-tert-butylcarbonyloxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-17-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 182 g / acetic acid / 4 h / 55 °C

2: 81 percent / imidazole / CH₂Cl₂ / 3 h / 20 °C

3: 69 percent / Ph₃P; diisopropy azodicarboxylate / dioxane / 16 h / 20 °C

4: 21.1 g / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

5: 98 percent / pyridine / 20 h / 70 °C

With pyridine; 1H-imidazole; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 3: Mitsunobu reaction;

DOI:10.1080/15257770500268673

upstream raw materials:

(+/-)-9-[(1-hydroxymethyl)(3-tert-butylcarbonyloxy)propyl]adenine

mono-4-methoxytrityl chloride

(+/-)-4-O-pivaloylbutane-1,2,4-triol

2,2-dimethyl-propionic acid 2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester

Downstream raw materials:

(+/-)-9-[(1-(4-monomethoxytrityl)aminomethyl)(3-(di-tert-butylcarbonyloxymethylphosphono)methoxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine

(+/-)-9-[(1-(4-monomethoxytrityl)oxymethyl)(3-(di-isopropyloxycarbonyloxymethylphosphono)methoxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine

(+/-)-9-[(1-(4-monomethoxytrityloxy)methyl)(3-(di-tert-butylcarbonyloxymethylphosphono)methoxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine

(+/-)-9-[(1-(4-monomethoxytritylamino)methyl)(3-(diisopropylphosphono)methoxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine

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