O⁶-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-N²-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine

Base Information

• Chemical Name: O⁶-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-N²-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine
• CAS No.: 120881-22-3
• Molecular Formula: C₅₅H₅₄N₆O₁₁
• Molecular Weight: 975.067

Synonyms:O⁶-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-N²-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine

Chemical Property of O⁶-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-N²-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine

Chemical Property:

Purity/Quality:

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Technology Process of O⁶-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-N²-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine

There total 10 articles about O⁶-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-N²-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine 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: 79.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + O6-(2-cyanoethyl)-N2-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine (120853-28-3) → O6-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-N2-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine (120881-22-3)

Guidance literature:

With pyridine; dmap; for 2h; Ambient temperature;

DOI:10.1021/jo00274a041

Reference yield:

3',5'-O-1,1,3,3-tetraisopropyldisiloxan-1,3-diyl-guanosine (69304-44-5) → O6-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-N2-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine (120881-22-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / dimethylformamide / 20 h / Ambient temperature

2: 2-mesitylenesulfonic acid / tetrahydrofuran / 3 h / Ambient temperature

3: methanol. NH₃ / CH₂Cl₂ / 24 h / Ambient temperature

4: 82 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / Ambient temperature

5: 1.) 1-methylpyrrolidine, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) CH₂Cl₂, RT, 1 h, 2.) a) -25 deg C, 20 min, b) 0 deg C, 1 h

6: pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

7: 77 percent / tetrabutylammonium fluoride, pyridine / tetrahydrofuran; H₂O / 2 h / Ambient temperature

8: 79 percent / pyridine, 4-(dimethylamino)pyridine / 2 h / Ambient temperature

With 1-Methylpyrrolidine; pyridine; dmap; mesitylene sulfonic acid; tetrabutyl ammonium fluoride; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00274a041

Reference yield:

4-methoxy-2,6-dihydropyran (17327-22-9) → O6-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-N2-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine (120881-22-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 2-mesitylenesulfonic acid / tetrahydrofuran / 3 h / Ambient temperature

2: methanol. NH₃ / CH₂Cl₂ / 24 h / Ambient temperature

3: 82 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / Ambient temperature

4: 1.) 1-methylpyrrolidine, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) CH₂Cl₂, RT, 1 h, 2.) a) -25 deg C, 20 min, b) 0 deg C, 1 h

5: pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

6: 77 percent / tetrabutylammonium fluoride, pyridine / tetrahydrofuran; H₂O / 2 h / Ambient temperature

7: 79 percent / pyridine, 4-(dimethylamino)pyridine / 2 h / Ambient temperature

With 1-Methylpyrrolidine; pyridine; dmap; mesitylene sulfonic acid; tetrabutyl ammonium fluoride; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00274a041

upstream raw materials:

4,4'-dimethoxytrityl chloride

O⁶-(2-cyanoethyl)-N²-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine

3',5'-O-1,1,3,3-tetraisopropyldisiloxan-1,3-diyl-guanosine

4-methoxy-2,6-dihydropyran

Downstream raw materials:

C₆₇H₆₁ClN₉O₁₄P

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