N⁴-acetyl-2'-O-[(3-bromopropoxy)methyl]-5'-O-(4,4'-dimethoxytrityl)cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite)

Base Information

• Chemical Name: N⁴-acetyl-2'-O-[(3-bromopropoxy)methyl]-5'-O-(4,4'-dimethoxytrityl)cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite)
• CAS No.: 289891-54-9
• Molecular Formula: C₄₅H₅₇BrN₅O₁₀P
• Molecular Weight: 938.853

Synonyms:N⁴-acetyl-2'-O-[(3-bromopropoxy)methyl]-5'-O-(4,4'-dimethoxytrityl)cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite)

Chemical Property of N⁴-acetyl-2'-O-[(3-bromopropoxy)methyl]-5'-O-(4,4'-dimethoxytrityl)cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite)

Chemical Property:

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Technology Process of N⁴-acetyl-2'-O-[(3-bromopropoxy)methyl]-5'-O-(4,4'-dimethoxytrityl)cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite)

There total 2 articles about N⁴-acetyl-2'-O-[(3-bromopropoxy)methyl]-5'-O-(4,4'-dimethoxytrityl)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: 89.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + N4-acetyl-2'-O-[(3-bromopropoxy)methyl]-5'-O-(4,4'-dimethoxytrityl)cytidine → N4-acetyl-2'-O-[(3-bromopropoxy)methyl]-5'-O-(4,4'-dimethoxytrityl)cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite) (289891-54-9)

Guidance literature:

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

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

Reference yield:

N4-acetyl-5'-O-(4,4'-dimethoxytrityl)cytidine (121058-82-0) → N4-acetyl-2'-O-[(3-bromopropoxy)methyl]-5'-O-(4,4'-dimethoxytrityl)cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite) (289891-54-9)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 45 percent / 1,2-dichloro-ethane / 70 °C

2.1: 89 percent / iPr₂NEt / CH₂Cl₂ / 20 °C

With dibutyltin chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1,2-dichloro-ethane; 1.1: Metallation / 1.2: Alkylation / 2.1: phosphorylation;

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

upstream raw materials:

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

N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)cytidine

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