ethyl 3-[(2S,4S)-2-(tert-butoxycarbonylaminomethyl)-4-(N³-benzoyl-thymin-1-yl)-pyrrolidin-1-yl]-propanoate

Base Information

• Chemical Name: ethyl 3-[(2S,4S)-2-(tert-butoxycarbonylaminomethyl)-4-(N³-benzoyl-thymin-1-yl)-pyrrolidin-1-yl]-propanoate
• CAS No.: 847994-39-2
• Molecular Formula: C₂₇H₃₆N₄O₇
• Molecular Weight: 528.605

Synonyms:ethyl 3-[(2S,4S)-2-(tert-butoxycarbonylaminomethyl)-4-(N³-benzoyl-thymin-1-yl)-pyrrolidin-1-yl]-propanoate

Chemical Property of ethyl 3-[(2S,4S)-2-(tert-butoxycarbonylaminomethyl)-4-(N³-benzoyl-thymin-1-yl)-pyrrolidin-1-yl]-propanoate

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Technology Process of ethyl 3-[(2S,4S)-2-(tert-butoxycarbonylaminomethyl)-4-(N³-benzoyl-thymin-1-yl)-pyrrolidin-1-yl]-propanoate

There total 11 articles about ethyl 3-[(2S,4S)-2-(tert-butoxycarbonylaminomethyl)-4-(N³-benzoyl-thymin-1-yl)-pyrrolidin-1-yl]-propanoate 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: 72.0%

ethyl 3-[(2S,4R)-2-(tert-butyloxycarbonylaminomethyl)-4-hydroxypyrrolidin-1-yl]-propanoate (847994-53-0) + N-3-benzoylthymine (4330-20-5) → ethyl 3-[(2S,4S)-2-(tert-butoxycarbonylaminomethyl)-4-(N3-benzoyl-thymin-1-yl)-pyrrolidin-1-yl]-propanoate (847994-39-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In benzene; at 20 ℃; for 5h;

DOI:10.1016/j.tet.2005.12.002

Reference yield:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) → ethyl 3-[(2S,4S)-2-(tert-butoxycarbonylaminomethyl)-4-(N3-benzoyl-thymin-1-yl)-pyrrolidin-1-yl]-propanoate (847994-39-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / LiCl; NaBH₄ / tetrahydrofuran; ethanol / 20 °C

2: 75 percent / pyridine / 8 h / 20 °C

3: 96 percent / NaN₃ / dimethylformamide / 8 h / 55 °C

4: H₂ / Raney Ni / methanol / 3.5 h / 20 °C / 1810.02 - 2068.59 Torr

5: 76 percent / Et₃N / dimethylsulfoxide / 8 h / 50 °C

6: H₂ / Pd/C / methanol / 7 h / 20 °C / 3102.89 Torr

7: 72 percent / methanol / 3 h / 20 °C

8: 72 percent / triphenylphosphine; DEAD / benzene / 5 h / 20 °C

With pyridine; sodium tetrahydroborate; sodium azide; hydrogen; triethylamine; triphenylphosphine; lithium chloride; diethylazodicarboxylate; palladium on activated charcoal; nickel; In tetrahydrofuran; methanol; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 8: Mitsunobu reaction;

DOI:10.1016/j.tet.2005.12.002

Reference yield:

(2S,4R)-N1-(benzyloxycarbonyl)-4-hydroxy-2-(hydroxymethyl)-pyrrolidine (95687-41-5,1448706-36-2) → ethyl 3-[(2S,4S)-2-(tert-butoxycarbonylaminomethyl)-4-(N3-benzoyl-thymin-1-yl)-pyrrolidin-1-yl]-propanoate (847994-39-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / pyridine / 8 h / 20 °C

2: 96 percent / NaN₃ / dimethylformamide / 8 h / 55 °C

3: H₂ / Raney Ni / methanol / 3.5 h / 20 °C / 1810.02 - 2068.59 Torr

4: 76 percent / Et₃N / dimethylsulfoxide / 8 h / 50 °C

5: H₂ / Pd/C / methanol / 7 h / 20 °C / 3102.89 Torr

6: 72 percent / methanol / 3 h / 20 °C

7: 72 percent / triphenylphosphine; DEAD / benzene / 5 h / 20 °C

With pyridine; sodium azide; hydrogen; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; nickel; In methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 7: Mitsunobu reaction;

DOI:10.1016/j.tet.2005.12.002

upstream raw materials:

ethyl 3-[(2S,4R)-2-(tert-butyloxycarbonylaminomethyl)-4-hydroxypyrrolidin-1-yl]-propanoate

N-3-benzoylthymine

(2S,4R)-2-(tert-butyloxycarbonylaminomethyl)-4-hydroxypyrrolidine

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

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