5'-O-(4,4'-Dimethoxytrityl)-2'-O-tert-butyldimethylsilyl-β-D-xylofuranosyl-N⁶-(N,N'-dimethylaminomethylene)adenine

Base Information

• Chemical Name: 5'-O-(4,4'-Dimethoxytrityl)-2'-O-tert-butyldimethylsilyl-β-D-xylofuranosyl-N⁶-(N,N'-dimethylaminomethylene)adenine
• CAS No.: 124492-56-4
• Molecular Formula: C₄₀H₅₀N₆O₆Si
• Molecular Weight: 738.959
• Mol file: 124492-56-4.mol

Synonyms:5'-O-(4,4'-Dimethoxytrityl)-2'-O-tert-butyldimethylsilyl-β-D-xylofuranosyl-N⁶-(N,N'-dimethylaminomethylene)adenine

Chemical Property of 5'-O-(4,4'-Dimethoxytrityl)-2'-O-tert-butyldimethylsilyl-β-D-xylofuranosyl-N⁶-(N,N'-dimethylaminomethylene)adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(4,4'-Dimethoxytrityl)-2'-O-tert-butyldimethylsilyl-β-D-xylofuranosyl-N⁶-(N,N'-dimethylaminomethylene)adenine

There total 5 articles about 5'-O-(4,4'-Dimethoxytrityl)-2'-O-tert-butyldimethylsilyl-β-D-xylofuranosyl-N⁶-(N,N'-dimethylaminomethylene)adenine 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: 61.0%

N'-{9-[(2R,3S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-tetrahydro-furan-2-yl]-9H-purin-6-yl}-N,N-dimethyl-formamidine (124492-54-2) → 5'-O-(4,4'-Dimethoxytrityl)-2'-O-tert-butyldimethylsilyl-β-D-xylofuranosyl-N6-(N,N'-dimethylaminomethylene)adenine (124492-56-4)

Guidance literature:

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran; at -18 ℃; for 2h;

DOI:10.1055/s-1989-27258

Reference yield:

N6-(N,N'-Dimethylaminomethylene)adenosine (17331-15-6) → 5'-O-(4,4'-Dimethoxytrityl)-2'-O-tert-butyldimethylsilyl-β-D-xylofuranosyl-N6-(N,N'-dimethylaminomethylene)adenine (124492-56-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / dimethylformamide; pyridine / 10 h / Ambient temperature

2: 80 percent / AgNO₃, pyridine / tetrahydrofuran / 2 h / Ambient temperature

3: 60 percent / pyridine, trifluoroacetic acid, dicyclohexylcarbodiimide / dimethylsulfoxide; benzene / 4 h / 13 °C

4: 61 percent / NaBH₄, Et₃N / tetrahydrofuran / 2 h / -18 °C

With pyridine; sodium tetrahydroborate; silver nitrate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; pyridine; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1055/s-1989-27258

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 5'-O-(4,4'-Dimethoxytrityl)-2'-O-tert-butyldimethylsilyl-β-D-xylofuranosyl-N6-(N,N'-dimethylaminomethylene)adenine (124492-56-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / dimethylformamide; pyridine / 10 h / Ambient temperature

2: 80 percent / AgNO₃, pyridine / tetrahydrofuran / 2 h / Ambient temperature

3: 60 percent / pyridine, trifluoroacetic acid, dicyclohexylcarbodiimide / dimethylsulfoxide; benzene / 4 h / 13 °C

4: 61 percent / NaBH₄, Et₃N / tetrahydrofuran / 2 h / -18 °C

With pyridine; sodium tetrahydroborate; silver nitrate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; pyridine; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1055/s-1989-27258

upstream raw materials:

N'-{9-[(2R,3S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-tetrahydro-furan-2-yl]-9H-purin-6-yl}-N,N-dimethyl-formamidine

N⁶-(N,N'-Dimethylaminomethylene)adenosine

4,4'-dimethoxytrityl chloride

5'-O-(4,4'-dimethoxytrityl)-N⁶-dimethylaminomethyleneadenosine