1-(N-[tert-butoxycarbonylaminoethyl])-(4S)-(N⁴-benzyloxycarbonylcytosin-1-yl)-2-(S)-proline methyl ester

Base Information

• Chemical Name: 1-(N-[tert-butoxycarbonylaminoethyl])-(4S)-(N⁴-benzyloxycarbonylcytosin-1-yl)-2-(S)-proline methyl ester
• CAS No.: 340961-34-4
• Molecular Formula: C₂₅H₃₃N₅O₇
• Molecular Weight: 515.566

Synonyms:1-(N-[tert-butoxycarbonylaminoethyl])-(4S)-(N⁴-benzyloxycarbonylcytosin-1-yl)-2-(S)-proline methyl ester

Chemical Property of 1-(N-[tert-butoxycarbonylaminoethyl])-(4S)-(N⁴-benzyloxycarbonylcytosin-1-yl)-2-(S)-proline methyl ester

Chemical Property:

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Technology Process of 1-(N-[tert-butoxycarbonylaminoethyl])-(4S)-(N⁴-benzyloxycarbonylcytosin-1-yl)-2-(S)-proline methyl ester

There total 2 articles about 1-(N-[tert-butoxycarbonylaminoethyl])-(4S)-(N⁴-benzyloxycarbonylcytosin-1-yl)-2-(S)-proline methyl 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: 60.0%

N-benzyloxycarbonyl cytosine (149411-91-6) + 1-(N-[2-(tert-butoxycarbonylamino)ethyl])-(4R)-O-mesyl-2-(S)-proline methyl ester (340961-32-2) → 1-(N-[tert-butoxycarbonylaminoethyl])-(4S)-(N4-benzyloxycarbonylcytosin-1-yl)-2-(S)-proline methyl ester (340961-34-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1021/ol015546k

Reference yield:

1-(N-[2-(tert-butoxycarbonylamino)ethyl])-4-(R)-hydroxy-2-(S)-proline methyl ester (253307-68-5) → 1-(N-[tert-butoxycarbonylaminoethyl])-(4S)-(N4-benzyloxycarbonylcytosin-1-yl)-2-(S)-proline methyl ester (340961-34-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / pyridine / 2 h / cooling

2: 30 percent / potassium carbonate; 18-crown-6 / dimethylformamide / 5 h / 70 °C

With pyridine; 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1021/jo034048h

Reference yield: 99.5%

1-(N-[tert-butoxycarbonylaminoethyl])-(4S)-(N4-benzyloxycarbonylcytosin-1-yl)-2-(S)-proline methyl ester (340961-34-4) → 1-(N-[tert-butoxycarbonylaminoethyl])-(4S)-(N4-benzyloxycarbonylcytosin-1-yl)-2-(S)pyrrolidine-2(S)-carboxylic acid

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃; for 0.166667h;

DOI:10.1021/jo034048h

upstream raw materials:

N-benzyloxycarbonyl cytosine

1-(N-[2-(tert-butoxycarbonylamino)ethyl])-(4R)-O-mesyl-2-(S)-proline methyl ester

1-(N-[2-(tert-butoxycarbonylamino)ethyl])-4-(R)-hydroxy-2-(S)-proline methyl ester

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