5'-O-(4,4'-dimethoxytrityl)-N⁴-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite)

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-N⁴-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite)
• CAS No.: 312709-91-4
• Molecular Formula: C₆₆H₉₆N₅O₁₂PSi₂
• Molecular Weight: 1238.66

Synonyms:5'-O-(4,4'-dimethoxytrityl)-N⁴-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite)

Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-N⁴-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite)

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Technology Process of 5'-O-(4,4'-dimethoxytrityl)-N⁴-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite)

There total 7 articles about 5'-O-(4,4'-dimethoxytrityl)-N⁴-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite) 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: 85.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + 5'-O-(4,4'-dimethoxytrityl)-N4-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine (312709-90-3) → 5'-O-(4,4'-dimethoxytrityl)-N4-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite) (312709-91-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 14h;

DOI:10.1002/1522-2675(20000906)83:9<2477::AID-HLCA2477>3.0.CO;2-9

Reference yield:

triisopropylsilyl chloride (13154-24-0) → 5'-O-(4,4'-dimethoxytrityl)-N4-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite) (312709-91-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / NaH / dimethylformamide / 0.5 h / -70 °C

2: Et₃N / toluene / 0.5 h / 20 °C

3: DMAP; iPr₂NEt / toluene / 5 h / 80 °C

4: 85 percent / iPr₂NEt / CH₂Cl₂ / 14 h / 20 °C

With dmap; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: Condensation / 2: Condensation / 3: Condensation / 4: Condensation;

DOI:10.1002/1522-2675(20000906)83:9<2477::AID-HLCA2477>3.0.CO;2-9

Reference yield:

salicylic alcohol (90-01-7) → 5'-O-(4,4'-dimethoxytrityl)-N4-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite) (312709-91-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / NaH / dimethylformamide / 0.5 h / -70 °C

2: Et₃N / toluene / 0.5 h / 20 °C

3: DMAP; iPr₂NEt / toluene / 5 h / 80 °C

4: 85 percent / iPr₂NEt / CH₂Cl₂ / 14 h / 20 °C

With dmap; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: Condensation / 2: Condensation / 3: Condensation / 4: Condensation;

DOI:10.1002/1522-2675(20000906)83:9<2477::AID-HLCA2477>3.0.CO;2-9

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

5'-O-(4,4'-dimethoxytrityl)-N⁴-{{{2-[(triisopropylsilyl)oxy]benzyl}oxy}carbonyl}-2'-O-{[(triisopropylsilyl)oxy]methyl}cytidine

triisopropylsilyl chloride

salicylic alcohol

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