benzyl (2-amino-9-((2R,3R,4R,5R)-3,4-bis(((benzyloxy)carbonyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)carbamate

Base Information

• Chemical Name: benzyl (2-amino-9-((2R,3R,4R,5R)-3,4-bis(((benzyloxy)carbonyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)carbamate
• CAS No.: 1373397-01-3
• Molecular Formula: C₃₄H₃₂N₆O₁₀
• Molecular Weight: 684.662

Synonyms:benzyl (2-amino-9-((2R,3R,4R,5R)-3,4-bis(((benzyloxy)carbonyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)carbamate

Chemical Property of benzyl (2-amino-9-((2R,3R,4R,5R)-3,4-bis(((benzyloxy)carbonyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)carbamate

Chemical Property:

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Useful:

Technology Process of benzyl (2-amino-9-((2R,3R,4R,5R)-3,4-bis(((benzyloxy)carbonyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)carbamate

There total 1 articles about benzyl (2-amino-9-((2R,3R,4R,5R)-3,4-bis(((benzyloxy)carbonyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)carbamate 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: 97.0%

→ benzyl (2-amino-9-((2R,3R,4R,5R)-3,4-bis(((benzyloxy)carbonyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)carbamate (1373397-01-3)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; at 0 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ol300777p

Reference yield: 95.0%

benzyl (2-amino-9-((2R,3R,4R,5R)-3,4-bis(((benzyloxy)carbonyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)carbamate (1373397-01-3) + (2S)-ethyl 2-(chloro(phenoxy)phosphorylamino)propanoate (245078-14-2) → (2S)-ethyl 2-(((((2R,3R,4R,5R)-5-(2-amino-6-(((benzyloxy)carbonyl)amino)-9H-purin-9-yl)-3,4-bis(((benzyloxy)carbonyl)oxy)tetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Guidance literature:

benzyl (2-amino-9-((2R,3R,4R,5R)-3,4-bis(((benzyloxy)carbonyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)carbamate; With tert-butylmagnesium chloride; In tetrahydrofuran; at -78 ℃; for 0.666667h; Inert atmosphere;

(2S)-ethyl 2-(chloro(phenoxy)phosphorylamino)propanoate; In tetrahydrofuran; at -78 - 20 ℃; for 9h; Inert atmosphere;

DOI:10.1021/ol300777p

Reference yield:

benzyl (2-amino-9-((2R,3R,4R,5R)-3,4-bis(((benzyloxy)carbonyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)carbamate (1373397-01-3) + (2S)-ethyl 2-(chloro(phenoxy)phosphorylamino)propanoate (245078-14-2) → (2S)-ethyl 2-(((((2R,3S,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Guidance literature:

Multi-step reaction with 2 steps

1.1: tert-butylmagnesium chloride / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere

1.2: 9 h / -78 - 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / ethanol; ethyl acetate / 3 h / 20 °C / 760.05 Torr

With palladium 10% on activated carbon; tert-butylmagnesium chloride; hydrogen; In tetrahydrofuran; ethanol; ethyl acetate;

DOI:10.1021/ol300777p

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