(2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-(3-{N²-acetyl-O⁶-[2-(4-nitrophenyl)ethyl]-9-guaninyl}propyl)oxazolidin-5-one

Base Information

• Chemical Name: (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-(3-{N²-acetyl-O⁶-[2-(4-nitrophenyl)ethyl]-9-guaninyl}propyl)oxazolidin-5-one
• CAS No.: 316353-09-0
• Molecular Formula: C₃₃H₃₇N₇O₈
• Molecular Weight: 659.699

Synonyms:(2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-(3-{N²-acetyl-O⁶-[2-(4-nitrophenyl)ethyl]-9-guaninyl}propyl)oxazolidin-5-one

Chemical Property of (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-(3-{N²-acetyl-O⁶-[2-(4-nitrophenyl)ethyl]-9-guaninyl}propyl)oxazolidin-5-one

Chemical Property:

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Technology Process of (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-(3-{N²-acetyl-O⁶-[2-(4-nitrophenyl)ethyl]-9-guaninyl}propyl)oxazolidin-5-one

There total 6 articles about (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-(3-{N²-acetyl-O⁶-[2-(4-nitrophenyl)ethyl]-9-guaninyl}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: 21.0%

benzyl (2S,4S)-2-(tert-butyl)-4-isobutyl-5-oxooxazolidine-3-carboxylate (163084-89-7) + 9-(2-iodoethyl)-N2-acetyl-O6-[2-(4-nitrophenyl)ethyl]guanine (316353-07-8) → 9-ethyl-N2-acetyl-O6-[2-(4-nitrophenyl)ethyl]guanine + (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-(3-{N2-acetyl-O6-[2-(4-nitrophenyl)ethyl]-9-guaninyl}propyl)oxazolidin-5-one (316353-09-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 14h;

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

Reference yield:

pivalaldehyde (630-19-3) → (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-(3-{N2-acetyl-O6-[2-(4-nitrophenyl)ethyl]-9-guaninyl}propyl)oxazolidin-5-one (316353-09-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: aq. NaOH / H₂O / 0.08 h

1.2: hexane / 24 h / Heating

2.1: CH₂Cl₂ / 0 - 20 °C

3.1: 38.19 g / oxone / acetonitrile; H₂O / 24 h / 20 °C

4.1: 95 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

5.1: 21 percent / AIBN; Bu₃SnH / toluene / 14 h / 80 °C

With Oxone; sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; water; toluene; acetonitrile;

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

Reference yield:

N2-acetyl-O6-(2-(p-nitrophenyl)ethyl)guanine (218152-30-8) → (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-(3-{N2-acetyl-O6-[2-(4-nitrophenyl)ethyl]-9-guaninyl}propyl)oxazolidin-5-one (316353-09-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / Ph₃P; i-PrO₂CN=NCO₂i-Pr / dioxane / 0 - 20 °C

2: 85 percent / NaI / acetone / Heating

3: 21 percent / AIBN; Bu₃SnH / toluene / 14 h / 80 °C

With 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tri-n-butyl-tin hydride; triphenylphosphine; sodium iodide; In 1,4-dioxane; acetone; toluene; 1: Mitsunobu reaction;

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

upstream raw materials:

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

9-(2-iodoethyl)-N²-acetyl-O⁶-[2-(4-nitrophenyl)ethyl]guanine

pivalaldehyde

N²-acetyl-O⁶-(2-(p-nitrophenyl)ethyl)guanine

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