N-[6-Hydroxy-9-((1R,3S,4R)-3-hydroxy-4-trityloxymethyl-cyclopentyl)-9H-purin-2-yl]-isobutyramide

Base Information

• Chemical Name: N-[6-Hydroxy-9-((1R,3S,4R)-3-hydroxy-4-trityloxymethyl-cyclopentyl)-9H-purin-2-yl]-isobutyramide
• CAS No.: 201848-20-6
• Molecular Formula: C₃₄H₃₅N₅O₄
• Molecular Weight: 577.683

Synonyms:N-[6-Hydroxy-9-((1R,3S,4R)-3-hydroxy-4-trityloxymethyl-cyclopentyl)-9H-purin-2-yl]-isobutyramide

Chemical Property of N-[6-Hydroxy-9-((1R,3S,4R)-3-hydroxy-4-trityloxymethyl-cyclopentyl)-9H-purin-2-yl]-isobutyramide

Chemical Property:

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Technology Process of N-[6-Hydroxy-9-((1R,3S,4R)-3-hydroxy-4-trityloxymethyl-cyclopentyl)-9H-purin-2-yl]-isobutyramide

There total 3 articles about N-[6-Hydroxy-9-((1R,3S,4R)-3-hydroxy-4-trityloxymethyl-cyclopentyl)-9H-purin-2-yl]-isobutyramide 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: 47.0%

N-{9-{(1R,3S,4R)-3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-trityloxymethyl-cyclopentyl}-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide → N-[6-Hydroxy-9-((1R,3S,4R)-3-hydroxy-4-trityloxymethyl-cyclopentyl)-9H-purin-2-yl]-isobutyramide (201848-20-6)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 25 ℃; for 120h;

DOI:10.1080/07328319708002566

Reference yield:

N2-Isobutyryl-O6-[2-(4-nitrophenylethyl)]guanine (143325-60-4) → N-[6-Hydroxy-9-((1R,3S,4R)-3-hydroxy-4-trityloxymethyl-cyclopentyl)-9H-purin-2-yl]-isobutyramide (201848-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / PPh₃, DEAD / dioxane; tetrahydrofuran / 20 h / 25 °C

2: 47 percent / acetic acid, TBAF / tetrahydrofuran / 120 h / 25 °C

With tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1080/07328319708002566

Reference yield:

(1S,3S,4R)-3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-trityloxymethyl-cyclopentanol (167260-21-1) → N-[6-Hydroxy-9-((1R,3S,4R)-3-hydroxy-4-trityloxymethyl-cyclopentyl)-9H-purin-2-yl]-isobutyramide (201848-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / PPh₃, DEAD / dioxane; tetrahydrofuran / 20 h / 25 °C

2: 47 percent / acetic acid, TBAF / tetrahydrofuran / 120 h / 25 °C

With tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1080/07328319708002566

upstream raw materials:

N²-Isobutyryl-O⁶-[2-(4-nitrophenylethyl)]guanine

(1S,3S,4R)-3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-trityloxymethyl-cyclopentanol

Downstream raw materials:

Acetic acid (1S,2R,4R)-4-(6-hydroxy-2-isobutyrylamino-purin-9-yl)-2-trityloxymethyl-cyclopentyl ester

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