(-)-5'-O-(12-aminododecanoyl)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine

Base Information

• Chemical Name: (-)-5'-O-(12-aminododecanoyl)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine
• CAS No.: 1373400-34-0
• Molecular Formula: C₄₁H₅₂N₄O₆S
• Molecular Weight: 728.953
• Mol file: 1373400-34-0.mol

Synonyms:(-)-5'-O-(12-aminododecanoyl)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine

Chemical Property of (-)-5'-O-(12-aminododecanoyl)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-5'-O-(12-aminododecanoyl)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine

There total 5 articles about (-)-5'-O-(12-aminododecanoyl)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine 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: 52.0%

(-)-5'-O-(12-(N-Fmoc-aminododecanoyl))-N(4)-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine (1373400-32-8) → (-)-5'-O-(12-aminododecanoyl)-N(4)-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine (1373400-34-0)

Guidance literature:

With piperidine; Octanethiol; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/jm300492q

Reference yield:

(-)-5'-O-(t-butyldimethylsilyl)-N(4)-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine (956896-99-4) → (-)-5'-O-(12-aminododecanoyl)-N(4)-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine (1373400-34-0)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutyl ammonium fluoride / 3 h

2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

3: piperidine; Octanethiol / tetrahydrofuran / 1 h / 20 °C

With piperidine; Octanethiol; tetrabutyl ammonium fluoride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm300492q

Reference yield:

(-)-5'-O-(t-butyldimethylsilyl)-2',3'-dideoxy-3'-thiacytidine (956896-97-2) → (-)-5'-O-(12-aminododecanoyl)-N(4)-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine (1373400-34-0)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 0 - 20 °C

2: tetrabutyl ammonium fluoride / 3 h

3: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

4: piperidine; Octanethiol / tetrahydrofuran / 1 h / 20 °C

With piperidine; pyridine; Octanethiol; tetrabutyl ammonium fluoride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm300492q

upstream raw materials:

(-)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine

9-fluorenylmethoxycarbonyl-12-aminododecanoic acid

(-)-5'-O-(t-butyldimethylsilyl)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine

(-)-5'-O-(12-(N-Fmoc-aminododecanoyl))-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine