[(2R,4R)-4-(6-Benzyloxycarbonylamino-purin-9-yl)-pyrrolidin-2-ylmethoxy]-acetic acid

Base Information

Chemical Name:[(2R,4R)-4-(6-Benzyloxycarbonylamino-purin-9-yl)-pyrrolidin-2-ylmethoxy]-acetic acid
CAS No.:289495-52-9
Molecular Formula:C₂₀H₂₂N₆O₅
Molecular Weight:426.432
Hs Code.:

Synonyms:[(2R,4R)-4-(6-Benzyloxycarbonylamino-purin-9-yl)-pyrrolidin-2-ylmethoxy]-acetic acid

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Chemical Property of [(2R,4R)-4-(6-Benzyloxycarbonylamino-purin-9-yl)-pyrrolidin-2-ylmethoxy]-acetic acid

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Technology Process of [(2R,4R)-4-(6-Benzyloxycarbonylamino-purin-9-yl)-pyrrolidin-2-ylmethoxy]-acetic acid

There total 9 articles about [(2R,4R)-4-(6-Benzyloxycarbonylamino-purin-9-yl)-pyrrolidin-2-ylmethoxy]-acetic acid 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: 60.0%

: 289495-51-8
4-(6-benzyloxycarbonylamino-purin-9-yl)-2-tert-butoxycarbonylmethoxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 289495-52-9
[(2R,4R)-4-(6-Benzyloxycarbonylamino-purin-9-yl)-pyrrolidin-2-ylmethoxy]-acetic acid

Guidance literature:: With trifluoroacetic acid; at 20 ℃; for 3h;
DOI:10.1016/S0960-894X(00)00121-9

Reference yield:

: 77450-02-3
N-(tert-butoxycarbonyl)-trans-4-hydroxy-D-proline ethyl ester

: 289495-52-9
[(2R,4R)-4-(6-Benzyloxycarbonylamino-purin-9-yl)-pyrrolidin-2-ylmethoxy]-acetic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / imidazole; Et₃N / dimethylformamide / 2 h / 20 °C

2: 86 percent / LiBH₄ / tetrahydrofuran / 2.5 h / 0 °C

3: 88 percent / Bu₄NHSO₄; NaOH / benzene / 2 h

4: 91 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

5: DEAD; Ph₃P / tetrahydrofuran / 49 h / 0 - 20 °C

6: conc. NH₃ / dioxane / 24 h / 60 °C

7: 70 percent / 16 h / 20 °C

8: 60 percent / CF₃COOH / 3 h / 20 °C

With 1H-imidazole; ammonium hydroxide; sodium hydroxide; lithium borohydride; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; benzene; 1: silylation / 2: Reduction / 3: Substitution / 4: desilylation / 5: Substitution / 6: amination / 7: Substitution / 8: Hydrolysis;
DOI:10.1016/S0960-894X(00)00121-9

Reference yield:

: 87-42-3
6-chloropurine

: 289495-52-9
[(2R,4R)-4-(6-Benzyloxycarbonylamino-purin-9-yl)-pyrrolidin-2-ylmethoxy]-acetic acid

Guidance literature:: Multi-step reaction with 4 steps

1: DEAD; Ph₃P / tetrahydrofuran / 49 h / 0 - 20 °C

2: conc. NH₃ / dioxane / 24 h / 60 °C

3: 70 percent / 16 h / 20 °C

4: 60 percent / CF₃COOH / 3 h / 20 °C

With ammonium hydroxide; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; 1: Substitution / 2: amination / 3: Substitution / 4: Hydrolysis;
DOI:10.1016/S0960-894X(00)00121-9