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

Base Information

• Chemical Name: allyl 3'-[N⁶-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenosyl] 5'-(3'-O-allyloxycarbonyl)thymidyl phosphite
• CAS No.: 181262-54-4
• Molecular Formula: C₅₂H₅₆N₇O₁₅P
• Molecular Weight: 1050.03

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 11 articles about allyl 3'-[N⁶-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenosyl] 5'-(3'-O-allyloxycarbonyl)thymidyl phosphite 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: 47.0%

Carbonic acid allyl ester (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (102423-19-8) + (3-{(2R,4S,5R)-4-(Allyloxy-diisopropylamino-phosphanyloxy)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-2-yl}-3H-purin-6-yl)-carbamic acid allyl ester (181262-51-1) → allyl 3'-[N6-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenosyl] 5'-(3'-O-allyloxycarbonyl)thymidyl phosphite (181262-54-4)

Guidance literature:

With 1H-tetrazole; In acetonitrile; at 25 ℃; for 2.5h;

DOI:10.1080/07328319608002437

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → allyl 3'-[N6-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenosyl] 5'-(3'-O-allyloxycarbonyl)thymidyl phosphite (181262-54-4)

Guidance literature:

Multi-step reaction with 6 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

With 1H-tetrazole; 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 3'-[N6-allyloxycarbonyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-3-isoadenosyl] 5'-(3'-O-allyloxycarbonyl)thymidyl phosphite (181262-54-4)

Guidance literature:

Multi-step reaction with 10 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

With 1H-tetrazole; 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:

Carbonic acid allyl ester (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

(3-{(2R,4S,5R)-4-(Allyloxy-diisopropylamino-phosphanyloxy)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-2-yl}-3H-purin-6-yl)-carbamic acid allyl ester

4,4'-dimethoxytrityl chloride

3-[beta-D-Ribofuranosyl]-adenine

Downstream raw materials:

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

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