(4S)-azido-(2R)-(N⁴-benzyloxycarbonylcytosin-1-ylmethyl)pyrrolidin-N-1-acetic acid ethyl ester

Base Information

• Chemical Name: (4S)-azido-(2R)-(N⁴-benzyloxycarbonylcytosin-1-ylmethyl)pyrrolidin-N-1-acetic acid ethyl ester
• CAS No.: 787615-27-4
• Molecular Formula: C₂₁H₂₅N₇O₅
• Molecular Weight: 455.473

Synonyms:(4S)-azido-(2R)-(N⁴-benzyloxycarbonylcytosin-1-ylmethyl)pyrrolidin-N-1-acetic acid ethyl ester

Chemical Property of (4S)-azido-(2R)-(N⁴-benzyloxycarbonylcytosin-1-ylmethyl)pyrrolidin-N-1-acetic acid ethyl ester

Chemical Property:

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Technology Process of (4S)-azido-(2R)-(N⁴-benzyloxycarbonylcytosin-1-ylmethyl)pyrrolidin-N-1-acetic acid ethyl ester

There total 3 articles about (4S)-azido-(2R)-(N⁴-benzyloxycarbonylcytosin-1-ylmethyl)pyrrolidin-N-1-acetic acid ethyl 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:

4-azido-2-(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (787615-25-2) → (4S)-azido-(2R)-(N4-benzyloxycarbonylcytosin-1-ylmethyl)pyrrolidin-N-1-acetic acid ethyl ester (787615-27-4)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂ / 0.17 h / 20 °C

2: 0.24 g / DIPEA / CH₂Cl₂; tetrahydrofuran / 3 h

With N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b407292h

Reference yield:

(2R,4S)-4-Azido-2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (418793-98-3) → (4S)-azido-(2R)-(N4-benzyloxycarbonylcytosin-1-ylmethyl)pyrrolidin-N-1-acetic acid ethyl ester (787615-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 30 percent / K₂CO₃; 18-crown-6 / dimethylformamide / 60 °C

2: TFA / CH₂Cl₂ / 0.17 h / 20 °C

3: 0.24 g / DIPEA / CH₂Cl₂; tetrahydrofuran / 3 h

With 18-crown-6 ether; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b407292h

Reference yield:

(2R,4S)-4-azido-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (418793-94-9) → (4S)-azido-(2R)-(N4-benzyloxycarbonylcytosin-1-ylmethyl)pyrrolidin-N-1-acetic acid ethyl ester (787615-27-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / triethylamine / CH₂Cl₂ / 20 °C

2: 30 percent / K₂CO₃; 18-crown-6 / dimethylformamide / 60 °C

3: TFA / CH₂Cl₂ / 0.17 h / 20 °C

4: 0.24 g / DIPEA / CH₂Cl₂; tetrahydrofuran / 3 h

With 18-crown-6 ether; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b407292h

upstream raw materials:

4-azido-2-(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

(2R,4S)-4-azido-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

(2R,4S)-4-Azido-2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

[2-(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-ylmethyl)-4-tert-butoxycarbonylamino-pyrrolidin-1-yl]-acetic acid ethyl ester

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