(2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-[3-(3-benzoyl-1-uracilyl)propyl]oxazolidin-5-one

Base Information

• Chemical Name: (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-[3-(3-benzoyl-1-uracilyl)propyl]oxazolidin-5-one
• CAS No.: 316352-83-7
• Molecular Formula: C₂₉H₃₁N₃O₇
• Molecular Weight: 533.581

Synonyms:(2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-[3-(3-benzoyl-1-uracilyl)propyl]oxazolidin-5-one

Chemical Property of (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-[3-(3-benzoyl-1-uracilyl)propyl]oxazolidin-5-one

Chemical Property:

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Technology Process of (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-[3-(3-benzoyl-1-uracilyl)propyl]oxazolidin-5-one

There total 2 articles about (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-[3-(3-benzoyl-1-uracilyl)propyl]oxazolidin-5-one 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: 47.0%

benzyl (2S,4S)-2-(tert-butyl)-4-isobutyl-5-oxooxazolidine-3-carboxylate (163084-89-7) + 1-(2-bromoethyl)-3-benzoyluracil (316352-79-1) → 3-benzoyl-1-ethyluracil (316352-69-9) + (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-[3-(3-benzoyl-1-uracilyl)propyl]oxazolidin-5-one (316352-83-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tributyltin chloride; sodium cyanoborohydride; In tert-butyl alcohol; for 7h; Heating;

DOI:10.1016/S0040-4020(01)00546-4

Reference yield:

3-benzoyl-1-(2-bromoethyl)pyrimidine-2,4(1H,3H)-dione (367493-18-3) → (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-[3-(3-benzoyl-1-uracilyl)propyl]oxazolidin-5-one (316352-83-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / NaI / acetone / Heating

2: 47 percent / Bu₃SnCl; NaBH₃CN; AIBN / 2-methyl-propan-2-ol / 7 h / Heating

With 2,2'-azobis(isobutyronitrile); tributyltin chloride; sodium cyanoborohydride; sodium iodide; In acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)00546-4

Reference yield:

(2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-[3-(3-benzoyl-1-uracilyl)propyl]oxazolidin-5-one (316352-83-7) → 5-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-benzyloxycarbonylamino-pentanoic acid (316353-15-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 0 ℃;

DOI:10.1039/b006843h

upstream raw materials:

benzyl (2S,4S)-2-(tert-butyl)-4-isobutyl-5-oxooxazolidine-3-carboxylate

1-(2-bromoethyl)-3-benzoyluracil

3-benzoyl-1-(2-bromoethyl)pyrimidine-2,4(1H,3H)-dione

Downstream raw materials:

5-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-benzyloxycarbonylamino-pentanoic acid

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