(+/-)-9-[(1-methylene)(3-phosphonomethoxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine

Base Information

• Chemical Name: (+/-)-9-[(1-methylene)(3-phosphonomethoxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine
• CAS No.: 889885-51-2
• Molecular Formula: C₃₀H₃₀N₅O₅P
• Molecular Weight: 571.572

Synonyms:(+/-)-9-[(1-methylene)(3-phosphonomethoxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine

Chemical Property of (+/-)-9-[(1-methylene)(3-phosphonomethoxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine

Chemical Property:

Purity/Quality:

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Technology Process of (+/-)-9-[(1-methylene)(3-phosphonomethoxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine

There total 8 articles about (+/-)-9-[(1-methylene)(3-phosphonomethoxy)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: 57.0%

(+/-)-9-[(1-methylene)(3-(diisopropylphosphono)methoxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-40-9) → (+/-)-9-[(1-methylene)(3-phosphonomethoxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-51-2)

Guidance literature:

With trimethylsilyl iodide; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 14h;

DOI:10.1080/15257770500268673

Reference yield:

(+/-)-9-[(1-hydroxymethyl)(3-tert-butylcarbonyloxy)propyl]adenine (889885-16-9) → (+/-)-9-[(1-methylene)(3-phosphonomethoxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-51-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 98 percent / pyridine / 20 h / 70 °C

2.1: 92 percent / NaOH / methanol; tetrahydrofuran / 16 h / 20 °C

3.1: 33 percent / NaH / dimethylformamide / 24 h / 20 °C

4.1: 55 percent / HCl / acetonitrile / 1 h / 20 °C

5.1: 76 percent / pyridine / 23 h / 20 °C

6.1: NaI / dimethylformamide / 6 h / 50 °C

6.2: 82 percent / DBU / dimethylformamide / 3 h / 80 °C

7.1: 57 percent / Et₃N; trimethylsilyliodide / dimethylformamide / 14 h / 20 °C

With pyridine; hydrogenchloride; sodium hydroxide; trimethylsilyl iodide; sodium hydride; triethylamine; sodium iodide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/15257770500268673

Reference yield:

(+/-)-9-[(1-tert-butyldimethylsilyloxymethyl)(3-pivaloyloxy)propyl]adenine (889885-15-8) → (+/-)-9-[(1-methylene)(3-phosphonomethoxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-51-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 21.1 g / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

2.1: 98 percent / pyridine / 20 h / 70 °C

3.1: 92 percent / NaOH / methanol; tetrahydrofuran / 16 h / 20 °C

4.1: 33 percent / NaH / dimethylformamide / 24 h / 20 °C

5.1: 55 percent / HCl / acetonitrile / 1 h / 20 °C

6.1: 76 percent / pyridine / 23 h / 20 °C

7.1: NaI / dimethylformamide / 6 h / 50 °C

7.2: 82 percent / DBU / dimethylformamide / 3 h / 80 °C

8.1: 57 percent / Et₃N; trimethylsilyliodide / dimethylformamide / 14 h / 20 °C

With pyridine; hydrogenchloride; sodium hydroxide; trimethylsilyl iodide; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; sodium iodide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/15257770500268673

upstream raw materials:

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

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

(+/-)-9-[(1-tert-butyldimethylsilyloxymethyl)(3-pivaloyloxy)propyl]adenine

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

Downstream raw materials:

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

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