1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]uracil

Base Information

• Chemical Name: 1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]uracil
• CAS No.: 289891-35-6
• Molecular Formula: C₄₆H₆₃BrN₂O₁₀Si
• Molecular Weight: 912.003

Synonyms:1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]uracil

Chemical Property of 1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]uracil

Chemical Property:

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Technology Process of 1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]uracil

There total 6 articles about 1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]uracil 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: 48.0%

chloromethoxy-triisopropyl-silane (217300-17-9) + 1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]uracil (289891-33-4) → 1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]uracil (289891-35-6) + 1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-3'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]uracil

Guidance literature:

1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]uracil; With dibutyltin chloride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 20 ℃; for 1.5h;

chloromethoxy-triisopropyl-silane; In 1,2-dichloro-ethane; at 75 ℃; for 0.25h;

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) → 1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]uracil (289891-35-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: AgNO₃; sym-collidine / CH₂Cl₂ / 1 h / 20 °C

2.1: 10N aq. NaOH / tetrahydrofuran; methanol; H₂O / 0.5 h / 20 °C

3.1: Bu₂SnCl₂; iPr₂NEt / 1,2-dichloro-ethane / 1.5 h / 20 °C

3.2: 48 percent / 1,2-dichloro-ethane / 0.25 h / 75 °C

With 2,4,6-trimethyl-pyridine; sodium hydroxide; dibutyltin chloride; silver nitrate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; 1.1: Alkylation / 2.1: debenzoylation / 3.1: Metallation / 3.2: Alkylation;

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

Reference yield:

1-[6'-O-(5-bromopentyl)-2',3'-di-O-benzoyl-β-D-allofuranosyl]uracil (289891-31-2) → 1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-allofuranosyl]uracil (289891-35-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: AgNO₃; sym-collidine / CH₂Cl₂ / 1 h / 20 °C

2.1: 10N aq. NaOH / tetrahydrofuran; methanol; H₂O / 0.5 h / 20 °C

3.1: Bu₂SnCl₂; iPr₂NEt / 1,2-dichloro-ethane / 1.5 h / 20 °C

3.2: 48 percent / 1,2-dichloro-ethane / 0.25 h / 75 °C

With 2,4,6-trimethyl-pyridine; sodium hydroxide; dibutyltin chloride; silver nitrate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; 1.1: Alkylation / 2.1: debenzoylation / 3.1: Metallation / 3.2: Alkylation;

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

upstream raw materials:

chloromethoxy-triisopropyl-silane

1-[6'-O-(5-bromopentyl)-5'-O-(4,4'-dimethoxytrityl)-β-D-allofuranosyl]uracil

4,4'-dimethoxytrityl chloride

1-[6'-O-(5-bromopentyl)-2',3'-di-O-benzoyl-β-D-allofuranosyl]uracil

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