(+/-)-N²-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)guanosine phosphoramidite

Base Information

• Chemical Name: (+/-)-N²-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)guanosine phosphoramidite
• CAS No.: 132183-41-6
• Molecular Formula: C₅₇H₅₈N₇O₇P
• Molecular Weight: 984.104

Synonyms:(+/-)-N²-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)guanosine phosphoramidite

Chemical Property of (+/-)-N²-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)guanosine phosphoramidite

Chemical Property:

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Technology Process of (+/-)-N²-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)guanosine phosphoramidite

There total 12 articles about (+/-)-N²-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)guanosine 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: 94.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + 2'-Deoxy-5'-(p-dimethoxytrityl)-N2-(1-pyrenylmethyl)guanosine (132209-53-1) → (+/-)-N2-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)guanosine phosphoramidite (132183-41-6)

Guidance literature:

With diisopropylamine; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jo00122a048

Reference yield:

pyrene-1-aldehyde (3029-19-4) → (+/-)-N2-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)guanosine phosphoramidite (132183-41-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / hydroxylamine*HCl, NaOH / aq. ethanol / 1.) reflux, 5 min, 2.) rt, 2 h

2: 85 percent / zinc, acetic acid / 15 h / Ambient temperature

3: 75 percent / triethylamine / dimethylformamide / 72 h / Ambient temperature

4: 98 percent / DBU, pyridine / Ambient temperature

5: 80 percent / pyridine / 2 h

6: 94 percent / diisopropylamine / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; sodium hydroxide; hydroxylamine hydrochloride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; zinc; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00122a048

Reference yield:

1-pyrene carboxaldehyde oxime (3786-56-9) → (+/-)-N2-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)guanosine phosphoramidite (132183-41-6)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 75 percent / triethylamine / dimethylformamide / 72 h / Ambient temperature

3: 98 percent / DBU, pyridine / Ambient temperature

4: 80 percent / pyridine / 2 h

5: 94 percent / diisopropylamine / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; zinc; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo00122a048

upstream raw materials:

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

2'-Deoxy-5'-(p-dimethoxytrityl)-N²-(1-pyrenylmethyl)guanosine

pyrene-1-aldehyde

1-pyrene carboxaldehyde oxime

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