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

Base Information

• Chemical Name: N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-L-prolyl)phosphoramidothioate]
• CAS No.: 651737-70-1
• Molecular Formula: C₄₄H₅₂N₇O₉PS
• Molecular Weight: 885.978

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 7 articles about N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-L-prolyl)phosphoramidothioate] 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: 59.0%

N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine (439097-93-5) + ethyl N,N-diisopropyl-N'-(N-trityl-L-prolyl)phosphorodiamidite (651737-61-0) → N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-L-prolyl)phosphoramidothioate] (651737-70-1)

Guidance literature:

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

With disulfiram; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1021/jo0351466

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-L-prolyl)phosphoramidothioate] (651737-70-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 5.58 g / triethylamine / methanol / 2 h / 20 °C

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

2.2: 59 percent / N,N,N',N'-tetraethylthiuram disulfide / acetonitrile / 3 h / 20 °C

With triethylamine; 1-methyl-5-mercaptotetrazole; In methanol; acetonitrile;

DOI:10.1021/jo0351466

Reference yield:

(S)-(-)-1-trityl-2-pyrrolidinecarboxamide (82935-40-8) → N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-L-prolyl)phosphoramidothioate] (651737-70-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 83 percent / N,N-diisopropylammonium 1H-tetrazolide / CH₂Cl₂ / 20 °C

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

2.2: 59 percent / N,N,N',N'-tetraethylthiuram disulfide / acetonitrile / 3 h / 20 °C

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

DOI:10.1021/jo0351466

upstream raw materials:

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

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

di-tert-butyl dicarbonate

(S)-(-)-1-trityl-2-pyrrolidinecarboxamide

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