2'-amino-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₄-(allyloxycarbonylaminoethyl)cytidine

Base Information

• Chemical Name: 2'-amino-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₄-(allyloxycarbonylaminoethyl)cytidine
• CAS No.: 1528642-23-0
• Molecular Formula: C₄₂H₅₅N₅O₈Si
• Molecular Weight: 786.013

Synonyms:2'-amino-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₄-(allyloxycarbonylaminoethyl)cytidine

Chemical Property of 2'-amino-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₄-(allyloxycarbonylaminoethyl)cytidine

Chemical Property:

Purity/Quality:

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Technology Process of 2'-amino-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₄-(allyloxycarbonylaminoethyl)cytidine

There total 6 articles about 2'-amino-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₄-(allyloxycarbonylaminoethyl)cytidine 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: 95.0%

2'-azido-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N4-(allyloxycarbonylaminoethyl)cytidine (1528642-20-7) → 2'-amino-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N4-(allyloxycarbonylaminoethyl)cytidine (1528642-23-0)

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1002/chem.201302972

Reference yield:

2'-azido-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine → 2'-amino-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N4-(allyloxycarbonylaminoethyl)cytidine (1528642-23-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trichlorophosphate / dichloromethane / 0.28 h / 0 °C / Inert atmosphere

1.2: 2.42 h / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

3.1: triphenylphosphine / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

With N-ethyl-N,N-diisopropylamine; triphenylphosphine; trichlorophosphate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.201302972

Reference yield:

2'-azido-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-4-(1,2,4-triazol-1-yl)uridine (1528642-08-1) → 2'-amino-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N4-(allyloxycarbonylaminoethyl)cytidine (1528642-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

2: triphenylphosphine / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

With N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/chem.201302972

upstream raw materials:

2'-azido-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-4-(1,2,4-triazol-1-yl)uridine

1-N-(allyloxycarbonyl)-1,2-diaminoethane

2'-azido-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₄-(allyloxycarbonylaminoethyl)cytidine

2'-azido-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine

Downstream raw materials:

2'-(anthraquinone-2-ylcarboxamido)-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₄-(allyloxycarbonylaminoethyl)cytidine

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