N²-acetyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]guanine

Base Information

• Chemical Name: N²-acetyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]guanine
• CAS No.: 289891-37-8
• Molecular Formula: C₄₉H₆₆BrN₅O₁₀Si
• Molecular Weight: 993.08

Synonyms:N²-acetyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]guanine

Chemical Property of N²-acetyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]guanine

Chemical Property:

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Technology Process of N²-acetyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]guanine

There total 4 articles about N²-acetyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]guanine 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: 55.0%

chloromethoxy-triisopropyl-silane (217300-17-9) + N2-acetyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]guanine → N2-acetyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]guanine (289891-37-8) + N2-acetyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-3'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]guanine

Guidance literature:

N²-acetyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]guanine; With dibutyltin chloride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 20 ℃;

chloromethoxy-triisopropyl-silane; In 1,2-dichloro-ethane; at 75 ℃;

DOI:10.1002/1522-2675(20000607)83:6<1127::AID-HLCA1127>3.0.CO;2-B

Reference yield:

N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide (19962-37-9) → N2-acetyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]guanine (289891-37-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 25 percent

2.1: Bu₂SnCl₂; iPr₂NEt / 1,2-dichloro-ethane / 20 °C

2.2: 55 percent / 1,2-dichloro-ethane / 75 °C

With dibutyltin chloride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; 2.1: Metallation / 2.2: Alkylation;

DOI:10.1002/1522-2675(20000607)83:6<1127::AID-HLCA1127>3.0.CO;2-B

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → N2-acetyl-9-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]guanine (289891-37-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 25 percent

2.1: Bu₂SnCl₂; iPr₂NEt / 1,2-dichloro-ethane / 20 °C

2.2: 55 percent / 1,2-dichloro-ethane / 75 °C

With dibutyltin chloride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; 2.1: Metallation / 2.2: Alkylation;

DOI:10.1002/1522-2675(20000607)83:6<1127::AID-HLCA1127>3.0.CO;2-B

upstream raw materials:

chloromethoxy-triisopropyl-silane

N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide

4,4'-dimethoxytrityl chloride

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