O⁶-allyl-N²-allyloxycarbonyl-3'-O-p-methoxytrityl-2'-deoxyguanosine 5'-(allyl N,N-diisopropylphosphoramidite)

Base Information

• Chemical Name: O⁶-allyl-N²-allyloxycarbonyl-3'-O-p-methoxytrityl-2'-deoxyguanosine 5'-(allyl N,N-diisopropylphosphoramidite)
• CAS No.: 232919-02-7
• Molecular Formula: C₄₆H₅₅N₆O₈P
• Molecular Weight: 850.952

Synonyms:O⁶-allyl-N²-allyloxycarbonyl-3'-O-p-methoxytrityl-2'-deoxyguanosine 5'-(allyl N,N-diisopropylphosphoramidite)

Chemical Property of O⁶-allyl-N²-allyloxycarbonyl-3'-O-p-methoxytrityl-2'-deoxyguanosine 5'-(allyl N,N-diisopropylphosphoramidite)

Chemical Property:

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Technology Process of O⁶-allyl-N²-allyloxycarbonyl-3'-O-p-methoxytrityl-2'-deoxyguanosine 5'-(allyl N,N-diisopropylphosphoramidite)

There total 4 articles about O⁶-allyl-N²-allyloxycarbonyl-3'-O-p-methoxytrityl-2'-deoxyguanosine 5'-(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: 74.0%

(allyloxy)bis(diisopropylamino)phosphine (108554-72-9) + O6-allyl-N2-allyloxycarbonyl-3'-O-p-methoxytrityl-2'-deoxyguanosine (357625-65-1) → O6-allyl-N2-allyloxycarbonyl-3'-O-p-methoxytrityl-2'-deoxyguanosine 5'-(allyl N,N-diisopropylphosphoramidite) (232919-02-7)

Guidance literature:

With 1H-tetrazole; diisopropylamine; In acetonitrile; at 25 ℃; for 2h;

DOI:10.1081/NCN-100002082

Reference yield:

O6-allyl-N2-[(allyloxy)carbonyl]-2'-deoxyguanosine (158391-96-9) → O6-allyl-N2-allyloxycarbonyl-3'-O-p-methoxytrityl-2'-deoxyguanosine 5'-(allyl N,N-diisopropylphosphoramidite) (232919-02-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / imidazole / dimethylformamide / 12 h / 25 °C

2: 71 percent / DBU / pyridine / 24 h / 25 °C

3: 100 percent / TBAF / tetrahydrofuran / 1.5 h / 25 °C

4: 74 percent / diisopropylamine; 1H-tetrazole / acetonitrile / 2 h / 25 °C

With 1H-imidazole; 1H-tetrazole; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1081/NCN-100002082

Reference yield:

{6-allyloxy-9-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-9H-purin-2-yl}-carbamic acid allyl ester (357625-73-1) → O6-allyl-N2-allyloxycarbonyl-3'-O-p-methoxytrityl-2'-deoxyguanosine 5'-(allyl N,N-diisopropylphosphoramidite) (232919-02-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / DBU / pyridine / 24 h / 25 °C

2: 100 percent / TBAF / tetrahydrofuran / 1.5 h / 25 °C

3: 74 percent / diisopropylamine; 1H-tetrazole / acetonitrile / 2 h / 25 °C

With 1H-tetrazole; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; In tetrahydrofuran; pyridine; acetonitrile;

DOI:10.1081/NCN-100002082

upstream raw materials:

(allyloxy)bis(diisopropylamino)phosphine

O⁶-allyl-N²-allyloxycarbonyl-3'-O-p-methoxytrityl-2'-deoxyguanosine

O⁶-allyl-N²-[(allyloxy)carbonyl]-2'-deoxyguanosine

{6-allyloxy-9-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-9H-purin-2-yl}-carbamic acid allyl ester

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