allyl [N⁶-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenylyl] (3'-5')-3'-O-allyloxycarbonylthymidine

Base Information

• Chemical Name: allyl [N⁶-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenylyl] (3'-5')-3'-O-allyloxycarbonylthymidine
• CAS No.: 181262-56-6
• Molecular Formula: C₅₂H₅₆N₇O₁₆P
• Molecular Weight: 1066.03

Synonyms:allyl [N⁶-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenylyl] (3'-5')-3'-O-allyloxycarbonylthymidine

Chemical Property of allyl [N⁶-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenylyl] (3'-5')-3'-O-allyloxycarbonylthymidine

Chemical Property:

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Technology Process of allyl [N⁶-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenylyl] (3'-5')-3'-O-allyloxycarbonylthymidine

There total 12 articles about allyl [N⁶-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenylyl] (3'-5')-3'-O-allyloxycarbonylthymidine 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: 91.0%

allyl 3'-[N6-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenosyl] 5'-(3'-O-allyloxycarbonyl)thymidyl phosphite (181262-54-4) → allyl [N6-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenylyl] (3'-5')-3'-O-allyloxycarbonylthymidine (181262-56-6)

Guidance literature:

With tert.-butylhydroperoxide; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1080/07328319608002437

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → allyl [N6-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenylyl] (3'-5')-3'-O-allyloxycarbonylthymidine (181262-56-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 45 percent / DMAP / pyridine / 0.5 h / 25 °C

2: 81 percent / DMAP, Et₃N / CH₂Cl₂; dimethylformamide / 12 h / 25 °C

3: 71 percent / tetrahydrofuran / 0.5 h / 25 °C

4: 79 percent / Bu₄NF, SiO₂ / tetrahydrofuran / 24 h / 25 °C

5: 69 percent / diisopropylamine, tetrazole / acetonitrile / 2 h / 25 °C

6: 47 percent / tetrazole / acetonitrile / 2.5 h / 25 °C

7: 91 percent / t-BuOOH / CH₂Cl₂ / 1 h / 0 °C

With 1H-tetrazole; tert.-butylhydroperoxide; dmap; tetrabutyl ammonium fluoride; silica gel; triethylamine; diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/07328319608002437

Reference yield:

3-[beta-D-Ribofuranosyl]-adenine (2273-78-1) → allyl [N6-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenylyl] (3'-5')-3'-O-allyloxycarbonylthymidine (181262-56-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 96 percent / pyridine / 6 h / 25 °C

2: 79 percent / tetrahydrofuran / 6 h / 25 °C

3: 76 percent / Bu₄SnCl, AIBN / toluene / 6 h / 75 °C

4: 91 percent / Bu₄NF / tetrahydrofuran / 4 h / 25 °C

5: 45 percent / DMAP / pyridine / 0.5 h / 25 °C

6: 81 percent / DMAP, Et₃N / CH₂Cl₂; dimethylformamide / 12 h / 25 °C

7: 71 percent / tetrahydrofuran / 0.5 h / 25 °C

8: 79 percent / Bu₄NF, SiO₂ / tetrahydrofuran / 24 h / 25 °C

9: 69 percent / diisopropylamine, tetrazole / acetonitrile / 2 h / 25 °C

10: 47 percent / tetrazole / acetonitrile / 2.5 h / 25 °C

11: 91 percent / t-BuOOH / CH₂Cl₂ / 1 h / 0 °C

With 1H-tetrazole; tert.-butylhydroperoxide; dmap; 2,2'-azobis(isobutyronitrile); Bu₄SnCl; tetrabutyl ammonium fluoride; silica gel; triethylamine; diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1080/07328319608002437

upstream raw materials:

allyl 3'-[N⁶-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenosyl] 5'-(3'-O-allyloxycarbonyl)thymidyl phosphite

4,4'-dimethoxytrityl chloride

3-[beta-D-Ribofuranosyl]-adenine

2'-deoxy-3-isoadenosine

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