(+/-)-N⁶-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)adenosine phosphoramidite

Base Information

• Chemical Name: (+/-)-N⁶-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)adenosine phosphoramidite
• CAS No.: 132183-10-9
• Molecular Formula: C₅₇H₅₈N₇O₆P
• Molecular Weight: 968.105

Synonyms:(+/-)-N⁶-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)adenosine phosphoramidite

Chemical Property of (+/-)-N⁶-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)adenosine phosphoramidite

Chemical Property:

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Technology Process of (+/-)-N⁶-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)adenosine phosphoramidite

There total 8 articles about (+/-)-N⁶-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)adenosine phosphoramidite 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: 99.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + 2'-deoxy-5-O-(4,4'-dimethoxytrityl)-N6-(pyren-1-ylmethy)adenosine (132183-40-5) → (+/-)-N6-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)adenosine phosphoramidite (132183-10-9)

Guidance literature:

With diisopropylamine; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1021/jo00122a048

Reference yield:

pyrene-1-aldehyde (3029-19-4) → (+/-)-N6-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)adenosine phosphoramidite (132183-10-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / AcOH / toluene / 6 h / Heating

2: 70 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

3: 90 percent / pyridine / 3 h / 20 °C

4: iPr₂EtN / acetonitrile; CH₂Cl₂ / 1 h / 20 °C

With pyridine; lithium aluminium tetrahydride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 1: Condensation / 2: Reduction / 3: Etherification / 4: Substitution;

DOI:10.1002/1522-2675(20000705)83:7<1408::AID-HLCA1408>3.0.CO;2-U

Reference yield:

1-pyrene carboxaldehyde oxime (3786-56-9) → (+/-)-N6-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)adenosine phosphoramidite (132183-10-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / zinc, acetic acid / 15 h / Ambient temperature

2: 63 percent / triethylamine / dimethylformamide / 72 h / Ambient temperature

3: 99 percent / NaOMe / methanol; tetrahydrofuran / 4 h / Ambient temperature

4: 95 percent / pyridine / 2 h

5: 99 percent / diisopropylamine / tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; sodium methylate; acetic acid; triethylamine; diisopropylamine; zinc; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00122a048

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

2'-deoxy-5-O-(4,4'-dimethoxytrityl)-N⁶-(pyren-1-ylmethy)adenosine

pyrene-1-aldehyde

4,4'-dimethoxytrityl chloride

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