N²-(dimethylaminomethylene)-2'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)guanosine 3'-[(2-cyanoethyl)-N,N-diisopropylaminophosphoramidite]

Base Information

• Chemical Name: N²-(dimethylaminomethylene)-2'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)guanosine 3'-[(2-cyanoethyl)-N,N-diisopropylaminophosphoramidite]
• CAS No.: 141913-05-5
• Molecular Formula: C₄₉H₆₇N₈O₈PSi
• Molecular Weight: 955.179

Synonyms:

Chemical Property of N²-(dimethylaminomethylene)-2'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)guanosine 3'-[(2-cyanoethyl)-N,N-diisopropylaminophosphoramidite]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N²-(dimethylaminomethylene)-2'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)guanosine 3'-[(2-cyanoethyl)-N,N-diisopropylaminophosphoramidite]

There total 8 articles about N²-(dimethylaminomethylene)-2'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)guanosine 3'-[(2-cyanoethyl)-N,N-diisopropylaminophosphoramidite] 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: 79.0%

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + N2-(dimethylaminomethylene)-2'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)guanosine (126922-61-0) → N2-(dimethylaminomethylene)-2'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)guanosine 3'-[(2-cyanoethyl)-N,N-diisopropylaminophosphoramidite] (149559-87-5,141913-02-2,141913-05-5)

Guidance literature:

With 1H-tetrazole; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1016/j.bmc.2010.07.068

Reference yield:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + N2-(dimethylaminomethylene)-2'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)guanosine (126922-61-0) → N2-(dimethylaminomethylene)-2'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)guanosine 3'-[(2-cyanoethyl)-N,N-diisopropylaminophosphoramidite] (149559-87-5,141913-02-2,141913-05-5)

Guidance literature:

With 1-methyl-1H-imidazole; 2,4,6-trimethyl-pyridine; In tetrahydrofuran; at 25 ℃; for 1h;

DOI:10.1246/bcsj.77.2089

Reference yield:

2'-O-(tert-butyldimethylsilyl)-2-N-(dimethylaminomethylene)guanosine (126922-63-2) → N2-(dimethylaminomethylene)-2'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)guanosine 3'-[(2-cyanoethyl)-N,N-diisopropylaminophosphoramidite] (149559-87-5,141913-02-2,141913-05-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 16 g / pyridine / 12 h / 25 °C

2: 2,4,6-collidine; N-methylimidazole / tetrahydrofuran / 1 h / 25 °C

With pyridine; 1-methyl-1H-imidazole; 2,4,6-trimethyl-pyridine; In tetrahydrofuran;

DOI:10.1246/bcsj.77.2089

upstream raw materials:

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

N²-(dimethylaminomethylene)-2'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)guanosine

2'-O-(tert-butyldimethylsilyl)-2-N-(dimethylaminomethylene)guanosine

N²-(dimethylaminomethylene)-2'-O-(tert-butyldimethylsilyl)-3',5'-O-(di-tert-butylsilanediyl)guanosine

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