N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-D-prolyl)phosphoramidate]

Base Information

• Chemical Name: N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-D-prolyl)phosphoramidate]
• CAS No.: 660851-67-2
• Molecular Formula: C₄₄H₅₂N₇O₁₀P
• Molecular Weight: 869.912

Synonyms:N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-D-prolyl)phosphoramidate]

Chemical Property of N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-D-prolyl)phosphoramidate]

Chemical Property:

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Technology Process of N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-D-prolyl)phosphoramidate]

There total 6 articles about N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-D-prolyl)phosphoramidate] 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: 83.0%

N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine (439097-93-5) + ethyl N,N-diisopropyl-N'-(N-trityl-D-prolyl)phosphorodiamidite (660851-66-1) → N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-D-prolyl)phosphoramidate] (660851-67-2)

Guidance literature:

N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine; ethyl N,N-diisopropyl-N'-(N-trityl-D-prolyl)phosphorodiamidite; With 1-methyl-5-mercaptotetrazole; In acetonitrile; at 20 ℃; for 1h;

With tert.-butylhydroperoxide; In decane; acetonitrile; at 20 ℃; for 0.166667h;

DOI:10.1021/jo0351466

Reference yield:

(R)-(+)-N-tritylprolinamine (146445-04-7) → N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-D-prolyl)phosphoramidate] (660851-67-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 76 percent / N,N-diisopropylammonium 1H-tetrazolide / CH₂Cl₂ / 3 h / 20 °C

2.1: 5-mercapto-1-methyl-1H-tetrazole / acetonitrile / 1 h / 20 °C

2.2: 83 percent / tert-butyl hydroperoxide / acetonitrile; decane / 0.17 h / 20 °C

With N,N-diisopropylamine tetrazolide; 1-methyl-5-mercaptotetrazole; In dichloromethane; acetonitrile;

DOI:10.1021/jo0351466

Reference yield:

8-bromoadenosine (2946-39-6) → N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-D-prolyl)phosphoramidate] (660851-67-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: acetic acid; sodium acetate / 3 h / 120 °C

2.1: 7.1 g / NaOH / ethanol / 3 h / 60 °C

3.1: p-toluenesulfonic acid monohydrate / acetone / 4 h / 20 °C

4.1: 5.58 g / triethylamine / methanol / 2 h / 20 °C

5.1: 5-mercapto-1-methyl-1H-tetrazole / acetonitrile / 1 h / 20 °C

5.2: 83 percent / tert-butyl hydroperoxide / acetonitrile; decane / 0.17 h / 20 °C

With sodium hydroxide; sodium acetate; toluene-4-sulfonic acid; acetic acid; triethylamine; 1-methyl-5-mercaptotetrazole; In methanol; ethanol; acetone; acetonitrile;

DOI:10.1021/jo0351466

upstream raw materials:

N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine

ethyl N,N-diisopropyl-N'-(N-trityl-D-prolyl)phosphorodiamidite

(R)-(+)-N-tritylprolinamine

8-bromoadenosine

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