(2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-{3-[N⁶-(2-methylpropionyl)-9-adeninyl]propyl}oxazolidin-5-one

Base Information

• Chemical Name: (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-{3-[N⁶-(2-methylpropionyl)-9-adeninyl]propyl}oxazolidin-5-one
• CAS No.: 316352-96-2
• Molecular Formula: C₂₇H₃₄N₆O₅
• Molecular Weight: 522.604

Synonyms:(2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-{3-[N⁶-(2-methylpropionyl)-9-adeninyl]propyl}oxazolidin-5-one

Chemical Property of (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-{3-[N⁶-(2-methylpropionyl)-9-adeninyl]propyl}oxazolidin-5-one

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-{3-[N⁶-(2-methylpropionyl)-9-adeninyl]propyl}oxazolidin-5-one

There total 7 articles about (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-{3-[N⁶-(2-methylpropionyl)-9-adeninyl]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: 26.0%

benzyl (2S,4S)-2-(tert-butyl)-4-isobutyl-5-oxooxazolidine-3-carboxylate (163084-89-7) + 9-(2-iodoethyl)-N6-(2-methylpropionyl)adenine (316352-92-8) → 9-ethyladenine (2715-68-6) + 9-ethyl-N6-(2-methylpropionyl)adenine + (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-[3-(9-adeninyl)propyl]oxazolidin-5-one (316352-98-4) + (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-{3-[N6-(2-methylpropionyl)-9-adeninyl]propyl}oxazolidin-5-one (316352-96-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tributyltin chloride; sodium cyanoborohydride; In tert-butyl alcohol; for 16h; Heating;

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

Reference yield:

(2S,4R)-benzyl 2-tert-butyl-4-(methylsulfonylmethyl)-5-oxooxazolidine-3-carboxylate (316352-58-6) → (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-{3-[N6-(2-methylpropionyl)-9-adeninyl]propyl}oxazolidin-5-one (316352-96-2)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 26 percent / Bu₃SnCl; NaBH₃CN; AIBN / 2-methyl-propan-2-ol / 16 h / Heating

With 2,2'-azobis(isobutyronitrile); tributyltin chloride; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; tert-butyl alcohol;

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

Reference yield:

pivalaldehyde (630-19-3) → (2S,4S)-3-benzyloxycarbonyl-2-tert-butyl-4-{3-[N6-(2-methylpropionyl)-9-adeninyl]propyl}oxazolidin-5-one (316352-96-2)

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: 26 percent / Bu₃SnCl; NaBH₃CN; AIBN / 2-methyl-propan-2-ol / 16 h / Heating

With Oxone; sodium hydroxide; 2,2'-azobis(isobutyronitrile); tributyltin chloride; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; water; acetonitrile; tert-butyl alcohol;

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)-N⁶-(2-methylpropionyl)adenine

pivalaldehyde

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

Downstream raw materials:

(2S)-benzyloxycarbonylamino-5-[N⁶-(2-methylpropionyl)-9-adeninyl]pentanoic acid

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