N²-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}isocytidine

Base Information

• Chemical Name: N²-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}isocytidine
• CAS No.: 872548-10-2
• Molecular Formula: C₄₂H₅₅N₃O₉Si
• Molecular Weight: 773.999

Synonyms:N²-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}isocytidine

Chemical Property of N²-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}isocytidine

Chemical Property:

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Technology Process of N²-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}isocytidine

There total 7 articles about N²-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}isocytidine 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: 12.0%

N2-acetyl-5'-O-(4,4'-dimethoxytrityl)isocytidine (872548-08-8) + chloromethoxy-triisopropyl-silane (217300-17-9) → N2-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}isocytidine (872548-10-2)

Guidance literature:

N²-acetyl-5'-O-(4,4'-dimethoxytrityl)isocytidine; With di-tert-butyltin dichloride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 20 ℃; for 0.5h;

chloromethoxy-triisopropyl-silane; In 1,2-dichloro-ethane; at 20 ℃; for 0.416667h;

DOI:10.1002/hlca.200590209

Reference yield:

5'-O-(4,4'-dimethoxytrityl)isocytidine (872548-05-5) → N2-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}isocytidine (872548-10-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / 1.5 h / 4 °C

2.1: DMAP / pyridine / 14 h / 20 °C

3.1: 1.81 g / Bu₄NF / tetrahydrofuran / 0.08 h / 20 °C

4.1: iPr₂NEt; tBu₂SnCl₂ / 1,2-dichloro-ethane / 0.5 h / 20 °C

4.2: 12 percent / 1,2-dichloro-ethane / 0.42 h / 20 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; di-tert-butyltin dichloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; 1,2-dichloro-ethane;

DOI:10.1002/hlca.200590209

Reference yield:

2-Amino-1-{(2R,3R,4R,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-furan-2-yl}-1H-pyrimidin-4-one → N2-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}isocytidine (872548-10-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: DMAP / pyridine / 14 h / 20 °C

2.1: 1.81 g / Bu₄NF / tetrahydrofuran / 0.08 h / 20 °C

3.1: iPr₂NEt; tBu₂SnCl₂ / 1,2-dichloro-ethane / 0.5 h / 20 °C

3.2: 12 percent / 1,2-dichloro-ethane / 0.42 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; di-tert-butyltin dichloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; 1,2-dichloro-ethane;

DOI:10.1002/hlca.200590209

upstream raw materials:

N²-acetyl-5'-O-(4,4'-dimethoxytrityl)isocytidine

chloromethoxy-triisopropyl-silane

5'-O-(4,4'-dimethoxytrityl)isocytidine

4,4'-dimethoxytrityl chloride

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