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

Base Information

• Chemical Name: N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-L-methionyl)phosphoramidate]
• CAS No.: 660851-80-9
• Molecular Formula: C₄₄H₅₄N₇O₁₀PS
• Molecular Weight: 903.993

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

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

Chemical Property:

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

There total 7 articles about N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-L-methionyl)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: 25.0%

N-trityl-L-methioninamide + N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N,N-diisopropylphosphoramidite] (660851-60-5) → N7-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N-(N-trityl-L-methionyl)phosphoramidate] (660851-80-9)

Guidance literature:

N-trityl-L-methioninamide; N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N,N-diisopropylphosphoramidite]; With 5-(3,5-dinitrophenyl)-1H-tetrazole; In acetonitrile; at 20 ℃; for 0.166667h;

With pyridine; water; iodine; In acetonitrile; at 20 ℃; for 0.333333h;

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-methionyl)phosphoramidate] (660851-80-9)

Guidance literature:

Multi-step reaction with 3 steps

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

2.1: 89 percent / N,N-diisopropylammonium 1H-tetrazolide / CH₂Cl₂ / 2 h / 20 °C

3.1: 5-(3,5-dinitrophenyl)-1H-tetrazole / acetonitrile / 0.17 h / 20 °C

3.2: 25 percent / iodine; pyridine; water / acetonitrile / 0.33 h / 20 °C

With N,N-diisopropylamine tetrazolide; triethylamine; 5-(3,5-dinitrophenyl)-1H-tetrazole; In methanol; 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-L-methionyl)phosphoramidate] (660851-80-9)

Guidance literature:

Multi-step reaction with 6 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: 89 percent / N,N-diisopropylammonium 1H-tetrazolide / CH₂Cl₂ / 2 h / 20 °C

6.1: 5-(3,5-dinitrophenyl)-1H-tetrazole / acetonitrile / 0.17 h / 20 °C

6.2: 25 percent / iodine; pyridine; water / acetonitrile / 0.33 h / 20 °C

With sodium hydroxide; N,N-diisopropylamine tetrazolide; sodium acetate; toluene-4-sulfonic acid; acetic acid; triethylamine; 5-(3,5-dinitrophenyl)-1H-tetrazole; In methanol; ethanol; dichloromethane; acetone; acetonitrile;

DOI:10.1021/jo0351466

upstream raw materials:

N⁷-tert-butoxycarbonyl-2',3'-O-isopropylidene-8-oxoadenosine 5'-[ethyl N,N-diisopropylphosphoramidite]

di-tert-butyl dicarbonate

8-bromoadenosine

2',3'-O-isopropylidene-8-oxoadenosine

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