N⁶-<(allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 3'-(allyl N,N-diisopropylphosphoramidite)

Base Information

• Chemical Name: N⁶-<(allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 3'-(allyl N,N-diisopropylphosphoramidite)
• CAS No.: 125138-92-3
• Molecular Formula: C₄₄H₅₃N₆O₈P
• Molecular Weight: 824.914

Synonyms:N⁶-<(allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 3'-(allyl N,N-diisopropylphosphoramidite)

Chemical Property of N⁶-<(allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 3'-(allyl N,N-diisopropylphosphoramidite)

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-<(allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 3'-(allyl N,N-diisopropylphosphoramidite)

There total 7 articles about N⁶-<(allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 3'-(allyl N,N-diisopropylphosphoramidite) 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: 91.0%

(allyloxy)bis(diisopropylamino)phosphine (108554-72-9) + N6-<(allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine (108554-88-7) → N6-<(allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 3'-(allyl N,N-diisopropylphosphoramidite) (125138-92-3)

Guidance literature:

With 1H-tetrazole; diisopropylamine; In acetonitrile; at 25 ℃; for 1.7h;

DOI:10.1021/ja00161a006

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → N6-<(allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 3'-(allyl N,N-diisopropylphosphoramidite) (125138-92-3)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N,4-dimethylaminopyridine, pyridine / 12 h / 13 °C

2: imidazole / dimethylformamide / 4.5 h / 13 °C

3: tetrahydrofuran / 3 h / 70 °C

4: 1.0 M tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 25 °C

5: 91 percent / diisopropylamine, 1H-tetrazole / acetonitrile / 1.7 h / 25 °C

With pyridine; 1H-imidazole; 1H-tetrazole; dmap; tetrabutyl ammonium fluoride; triethylamine; diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00161a006

Reference yield:

5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxyadenosine (17331-22-5) → N6-<(allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 3'-(allyl N,N-diisopropylphosphoramidite) (125138-92-3)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / 4.5 h / 13 °C

2: tetrahydrofuran / 3 h / 70 °C

3: 1.0 M tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 25 °C

4: 91 percent / diisopropylamine, 1H-tetrazole / acetonitrile / 1.7 h / 25 °C

With 1H-imidazole; 1H-tetrazole; tetrabutyl ammonium fluoride; diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00161a006

upstream raw materials:

(allyloxy)bis(diisopropylamino)phosphine

N⁶-<(allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine

4,4'-dimethoxytrityl chloride

5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxyadenosine

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