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

Base Information

Chemical Name:4-(6-benzyloxycarbonylamino-purin-9-yl)-2-tert-butoxycarbonylmethoxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:289495-51-8
Molecular Formula:C₂₉H₃₈N₆O₇
Molecular Weight:582.657
Hs Code.:

4-(6-benzyloxycarbonylamino-purin-9-yl)-2-<i>tert</i>-butoxycarbonylmethoxymethyl-pyrrolidine-1-carboxylic acid <i>tert</i>-butyl ester

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

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Chemical Property of 4-(6-benzyloxycarbonylamino-purin-9-yl)-2-tert-butoxycarbonylmethoxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of 4-(6-benzyloxycarbonylamino-purin-9-yl)-2-tert-butoxycarbonylmethoxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 9 articles about 4-(6-benzyloxycarbonylamino-purin-9-yl)-2-tert-butoxycarbonylmethoxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 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: 70.0%

: Rapaport reagent

: 289495-49-4
N-α-tert-butyloxycarbonyl-(2R,4R)-2-tert-butyloxycarbonylmethoxymethyl-4-(adenin-9'yl)-pyrrolidine

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

Guidance literature:: at 20 ℃; for 16h;
DOI:10.1016/S0960-894X(00)00121-9

Reference yield:

: 5292-43-3
bromoacetic acid tert-butyl ester

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

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / Bu₄NHSO₄; NaOH / benzene / 2 h

2: 91 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

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

4: conc. NH₃ / dioxane / 24 h / 60 °C

5: 70 percent / 16 h / 20 °C

With ammonium hydroxide; sodium hydroxide; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; benzene; 1: Substitution / 2: desilylation / 3: Substitution / 4: amination / 5: Substitution;
DOI:10.1016/S0960-894X(00)00121-9

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; ammonium hydroxide; sodium hydroxide; lithium borohydride; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; triethylamine; triphenylphosphine; 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;
DOI:10.1016/S0960-894X(00)00121-9