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

Base Information

• Chemical Name: (+/-)-9-[(1-azidomethyl)(3-(di-tert-butylcarbonyloxymethylphosphono)methoxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine
• CAS No.: 889885-54-5
• Molecular Formula: C₄₂H₅₁N₈O₉P
• Molecular Weight: 842.889

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

Chemical Property of (+/-)-9-[(1-azidomethyl)(3-(di-tert-butylcarbonyloxymethylphosphono)methoxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine

Chemical Property:

Purity/Quality:

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Technology Process of (+/-)-9-[(1-azidomethyl)(3-(di-tert-butylcarbonyloxymethylphosphono)methoxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine

There total 9 articles about (+/-)-9-[(1-azidomethyl)(3-(di-tert-butylcarbonyloxymethylphosphono)methoxy)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: 56.0%

(+/-)-9-[(1-azidomethyl)(3-phosphonomethoxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-46-5) + Chloromethyl pivalate (18997-19-8) → (+/-)-9-[(1-azidomethyl)(3-(di-tert-butylcarbonyloxymethylphosphono)methoxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-54-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 72h;

DOI:10.1080/15257770500268673

Reference yield:

(+/-)-9-[(1-hydroxymethyl)(3-tert-butylcarbonyloxy)propyl]adenine (889885-16-9) → (+/-)-9-[(1-azidomethyl)(3-(di-tert-butylcarbonyloxymethylphosphono)methoxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-54-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / pyridine / 20 h / 70 °C

2: 92 percent / NaOH / methanol; tetrahydrofuran / 16 h / 20 °C

3: 33 percent / NaH / dimethylformamide / 24 h / 20 °C

4: 55 percent / HCl / acetonitrile / 1 h / 20 °C

5: pyridine / 20 h / 20 °C

6: NaN₃ / dimethylformamide / 4 h / 100 °C

7: Et₃N; trimethylsilyliodide / dimethylformamide / 14 h / 20 °C

8: 56 percent / Et₃N / dimethylformamide / 72 h / 20 °C

With pyridine; hydrogenchloride; sodium hydroxide; sodium azide; trimethylsilyl iodide; sodium hydride; triethylamine; 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-azidomethyl)(3-(di-tert-butylcarbonyloxymethylphosphono)methoxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-54-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 21.1 g / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

2: 98 percent / pyridine / 20 h / 70 °C

3: 92 percent / NaOH / methanol; tetrahydrofuran / 16 h / 20 °C

4: 33 percent / NaH / dimethylformamide / 24 h / 20 °C

5: 55 percent / HCl / acetonitrile / 1 h / 20 °C

6: pyridine / 20 h / 20 °C

7: NaN₃ / dimethylformamide / 4 h / 100 °C

8: Et₃N; trimethylsilyliodide / dimethylformamide / 14 h / 20 °C

9: 56 percent / Et₃N / dimethylformamide / 72 h / 20 °C

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

DOI:10.1080/15257770500268673

upstream raw materials:

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

Chloromethyl pivalate

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

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

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