3'-amino-3'-deoxy-3'-[N-(9-fluorenylmethoxycarbonyl)-L-phenylalanyl]-5'-O-(p,p'-dimethoxytrityl)-N⁶,N⁶-dimethyladenosine

Base Information

• Chemical Name: 3'-amino-3'-deoxy-3'-[N-(9-fluorenylmethoxycarbonyl)-L-phenylalanyl]-5'-O-(p,p'-dimethoxytrityl)-N⁶,N⁶-dimethyladenosine
• CAS No.: 833447-54-4
• Molecular Formula: C₅₇H₅₅N₇O₈
• Molecular Weight: 966.106

Synonyms:3'-amino-3'-deoxy-3'-[N-(9-fluorenylmethoxycarbonyl)-L-phenylalanyl]-5'-O-(p,p'-dimethoxytrityl)-N⁶,N⁶-dimethyladenosine

Chemical Property of 3'-amino-3'-deoxy-3'-[N-(9-fluorenylmethoxycarbonyl)-L-phenylalanyl]-5'-O-(p,p'-dimethoxytrityl)-N⁶,N⁶-dimethyladenosine

Chemical Property:

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Technology Process of 3'-amino-3'-deoxy-3'-[N-(9-fluorenylmethoxycarbonyl)-L-phenylalanyl]-5'-O-(p,p'-dimethoxytrityl)-N⁶,N⁶-dimethyladenosine

There total 3 articles about 3'-amino-3'-deoxy-3'-[N-(9-fluorenylmethoxycarbonyl)-L-phenylalanyl]-5'-O-(p,p'-dimethoxytrityl)-N⁶,N⁶-dimethyladenosine 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: 86.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 3'-amino-3'-deoxy-3'-[N-(9-fluorenylmethoxycarbonyl)-L-phenylalanyl]-N6,N6-dimethyladenosine (833447-52-2) → 3'-amino-3'-deoxy-3'-[N-(9-fluorenylmethoxycarbonyl)-L-phenylalanyl]-5'-O-(p,p'-dimethoxytrityl)-N6,N6-dimethyladenosine (833447-54-4)

Guidance literature:

With pyridine; triethylamine; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2004.10.023

Reference yield:

N-Fmoc L-Phe (35661-40-6) → 3'-amino-3'-deoxy-3'-[N-(9-fluorenylmethoxycarbonyl)-L-phenylalanyl]-5'-O-(p,p'-dimethoxytrityl)-N6,N6-dimethyladenosine (833447-54-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / N-hydroxysuccinimide; EDCI / dimethylformamide / 0 - 20 °C

2: 86 percent / pyridine; triethylamine / 3 h / 20 °C

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.10.023

Reference yield:

3'-amino-3'-deoxy-N6,N6-dimethyladenosine (58-60-6) → 3'-amino-3'-deoxy-3'-[N-(9-fluorenylmethoxycarbonyl)-L-phenylalanyl]-5'-O-(p,p'-dimethoxytrityl)-N6,N6-dimethyladenosine (833447-54-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / N-hydroxysuccinimide; EDCI / dimethylformamide / 0 - 20 °C

2: 86 percent / pyridine; triethylamine / 3 h / 20 °C

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.10.023

upstream raw materials:

4,4'-dimethoxytrityl chloride

3'-amino-3'-deoxy-3'-[N-(9-fluorenylmethoxycarbonyl)-L-phenylalanyl]-N⁶,N⁶-dimethyladenosine

N-Fmoc L-Phe

3'-amino-3'-deoxy-N⁶,N⁶-dimethyladenosine

Downstream raw materials:

3'-amino-3'-deoxy-3'-[N-(9-fluorenylmethoxycarbonyl)-L-phenylalanyl]-5'-O-(p,p'-dimethoxytrityl)-N⁶,N⁶-dimethyladenosine 2'-O-succinate

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