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

Base Information

• Chemical Name: (+/-)-9-[(1-(4-monomethoxytritylamino)methyl)(3-(diisopropylphosphono)methoxy)propyl]-N⁶-(4-monomethoxytrityl)-adenine
• CAS No.: 889885-23-8
• Molecular Formula: C₅₆H₆₁N₆O₆P
• Molecular Weight: 945.111

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

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

Chemical Property:

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

There total 9 articles about (+/-)-9-[(1-(4-monomethoxytritylamino)methyl)(3-(diisopropylphosphono)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: 69.0%

(+/-)-9-[(1-aminomethyl)(3-(diisopropylphosphono)methoxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-22-7) + mono-4-methoxytrityl chloride (14470-28-1) → (+/-)-9-[(1-(4-monomethoxytritylamino)methyl)(3-(diisopropylphosphono)methoxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-23-8)

Guidance literature:

With pyridine; at 70 ℃; for 20h;

DOI:10.1080/15257770500268673

Reference yield:

(+/-)-9-[(1-hydroxymethyl)(3-tert-butylcarbonyloxy)propyl]adenine (889885-16-9) → (+/-)-9-[(1-(4-monomethoxytritylamino)methyl)(3-(diisopropylphosphono)methoxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-23-8)

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: 0.687 g / Ph₃P; H₂O / tetrahydrofuran / 15 h / 20 °C

8: 69 percent / pyridine / 20 h / 70 °C

With pyridine; hydrogenchloride; sodium hydroxide; sodium azide; water; sodium hydride; triphenylphosphine; 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-(4-monomethoxytritylamino)methyl)(3-(diisopropylphosphono)methoxy)propyl]-N6-(4-monomethoxytrityl)-adenine (889885-23-8)

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: 0.687 g / Ph₃P; H₂O / tetrahydrofuran / 15 h / 20 °C

9: 69 percent / pyridine / 20 h / 70 °C

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

DOI:10.1080/15257770500268673

upstream raw materials:

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

mono-4-methoxytrityl chloride

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

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

Downstream raw materials:

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

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

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