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

Base Information

• Chemical Name: 2'-(anthraquinone-2-ylcarboxamido)-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₄-(allyloxycarbonylaminoethyl)cytidine
• CAS No.: 1528642-26-3
• Molecular Formula: C₅₇H₆₁N₅O₁₁Si
• Molecular Weight: 1020.22
• Mol file: 1528642-26-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 2'-(anthraquinone-2-ylcarboxamido)-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: 90.0%

anthraquinone-2-carboxylic acid (117-78-2) + 2'-amino-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N4-(allyloxycarbonylaminoethyl)cytidine (1528642-23-0) → 2'-(anthraquinone-2-ylcarboxamido)-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N4-(allyloxycarbonylaminoethyl)cytidine (1528642-26-3)

Guidance literature:

anthraquinone-2-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.333333h; Inert atmosphere;

2'-amino-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N₄-(allyloxycarbonylaminoethyl)cytidine; In dichloromethane; at 0 - 20 ℃; for 12.0333h;

DOI:10.1002/chem.201302972

Reference yield:

2'-azido-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine → 2'-(anthraquinone-2-ylcarboxamido)-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N4-(allyloxycarbonylaminoethyl)cytidine (1528642-26-3)

Guidance literature:

Multi-step reaction with 4 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

4.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

4.2: 12.03 h / 0 - 20 °C

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 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'-(anthraquinone-2-ylcarboxamido)-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N4-(allyloxycarbonylaminoethyl)cytidine (1528642-26-3)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

3.2: 12.03 h / 0 - 20 °C

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 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

anthraquinone-2-carboxylic acid