(2'R,4'R)-2'-[(fluoren-9-yl-methoxycarbonyl)aminomethyl]-4'-(N⁶-benzoyladenin-9-yl)-N₁'-(tert-butoxycarbonylmethyl)-pyrrolidine

Base Information

• Chemical Name: (2'R,4'R)-2'-[(fluoren-9-yl-methoxycarbonyl)aminomethyl]-4'-(N⁶-benzoyladenin-9-yl)-N₁'-(tert-butoxycarbonylmethyl)-pyrrolidine
• CAS No.: 718632-80-5
• Molecular Formula: C₃₈H₃₉N₇O₅
• Molecular Weight: 673.772

Synonyms:(2'R,4'R)-2'-[(fluoren-9-yl-methoxycarbonyl)aminomethyl]-4'-(N⁶-benzoyladenin-9-yl)-N₁'-(tert-butoxycarbonylmethyl)-pyrrolidine

Chemical Property of (2'R,4'R)-2'-[(fluoren-9-yl-methoxycarbonyl)aminomethyl]-4'-(N⁶-benzoyladenin-9-yl)-N₁'-(tert-butoxycarbonylmethyl)-pyrrolidine

Chemical Property:

Purity/Quality:

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Technology Process of (2'R,4'R)-2'-[(fluoren-9-yl-methoxycarbonyl)aminomethyl]-4'-(N⁶-benzoyladenin-9-yl)-N₁'-(tert-butoxycarbonylmethyl)-pyrrolidine

There total 12 articles about (2'R,4'R)-2'-[(fluoren-9-yl-methoxycarbonyl)aminomethyl]-4'-(N⁶-benzoyladenin-9-yl)-N₁'-(tert-butoxycarbonylmethyl)-pyrrolidine 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: 61.0%

9-fluorenylmethyl N-succinimidyl carbonate (102774-86-7) + (2'R,4'R)-2'-aminomethyl-4'-(N6-benzoyladenin-9-yl)-N1'-(tert-butoxycarbonylmethyl)-pyrrolidine (927198-64-9) → (2'R,4'R)-2'-[(fluoren-9-yl-methoxycarbonyl)aminomethyl]-4'-(N6-benzoyladenin-9-yl)-N1'-(tert-butoxycarbonylmethyl)-pyrrolidine (718632-80-5)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; at 20 ℃; for 4h;

DOI:10.1039/b613384n

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (2'R,4'R)-2'-aminomethyl-4'-(N6-benzoyladenin-9-yl)-N1'-(tert-butoxycarbonylmethyl)-pyrrolidine (927198-64-9) → (2'R,4'R)-2'-[(fluoren-9-yl-methoxycarbonyl)aminomethyl]-4'-(N6-benzoyladenin-9-yl)-N1'-(tert-butoxycarbonylmethyl)-pyrrolidine (718632-80-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 18h;

DOI:10.1039/b315768g

Reference yield:

(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (114676-60-7) → (2'R,4'R)-2'-[(fluoren-9-yl-methoxycarbonyl)aminomethyl]-4'-(N6-benzoyladenin-9-yl)-N1'-(tert-butoxycarbonylmethyl)-pyrrolidine (718632-80-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 57 percent / NaN₃ / dimethylformamide / 16 h / 80 °C

2: 99 percent / HCl / dioxane; CH₂Cl₂ / 2.25 h / 0 - 20 °C

3: 94 percent / diisopropylethyl amine / CH₂Cl₂ / 24 h / 0 - 20 °C

4: 80 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 18 h / -30 - 20 °C

5: 92 percent / aq. NH₃ / methanol / 2 h

6: 86 percent / pyridine / 18 h

7: 37 percent / K₂CO₃; 18-crown-6 / dimethylformamide / 18 h / 80 °C

8: aq. H₂S; pyridine / 18 h

9: diisopropylethylamine / CH₂Cl₂ / 18 h / 0 °C

With pyridine; hydrogenchloride; ammonium hydroxide; sodium azide; 18-crown-6 ether; di-isopropyl azodicarboxylate; hydrogen sulfide; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; 4: Mitsunobu reaction;

DOI:10.1039/b315768g

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

(2'R,4'R)-2'-aminomethyl-4'-(N⁶-benzoyladenin-9-yl)-N₁'-(tert-butoxycarbonylmethyl)-pyrrolidine

9-fluorenylmethyl N-succinimidyl carbonate

(2R,4R)-tert-butyl 4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

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