(1'S,2'R,3'S)-N³-benzoyl-1-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]uracil

Base Information

• Chemical Name: (1'S,2'R,3'S)-N³-benzoyl-1-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]uracil
• CAS No.: 377748-61-3
• Molecular Formula: C₂₄H₂₈N₂O₆
• Molecular Weight: 440.496

Synonyms:(1'S,2'R,3'S)-N³-benzoyl-1-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]uracil

Chemical Property of (1'S,2'R,3'S)-N³-benzoyl-1-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]uracil

Chemical Property:

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Technology Process of (1'S,2'R,3'S)-N³-benzoyl-1-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]uracil

There total 10 articles about (1'S,2'R,3'S)-N³-benzoyl-1-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]uracil 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: 64.0%

3-N-benzoyluracil (2775-87-3) + (1R,2R,3S)-2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-ol (377748-53-3) → (1'S,2'R,3'S)-N3-benzoyl-1-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]uracil (377748-61-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1021/jm010256v

Reference yield:

tert-butyl methyl ether (1634-04-4) → (1'S,2'R,3'S)-N3-benzoyl-1-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]uracil (377748-61-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran; cyclohexane / 2 h / 0 °C

1.2: 61 percent / tetrahydrofuran; cyclohexane / 2 h / 0 °C

2.1: 30 percent / aq. H₂O₂; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 93 percent / NaBH₄; CeCl₃*7H₂O / methanol / 1 h / 0 °C

4.1: 64 percent / diethyl azadicarboxylate (DEAD); PPh₃ / tetrahydrofuran / 16 h / 20 °C

With pyridine; sodium tetrahydroborate; cerium(III) chloride; dihydrogen peroxide; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; cyclohexane;

DOI:10.1021/jm010256v

Reference yield:

(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one (115509-13-2) → (1'S,2'R,3'S)-N3-benzoyl-1-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]uracil (377748-61-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: t-BuOK; sec-BuLi / hexane / 3.5 h / -70 °C

1.2: 78 percent / tetrahydrofuran; hexane / 3 h / -70 °C

2.1: 94 percent / DMAP; Et₃N / CH₂Cl₂ / 24 h / 20 °C

3.1: 91 percent / PdCl₂(CH₃CN)2; p-benzoquinone / tetrahydrofuran / 24 h / Heating

4.1: 87 percent / K₂CO₃ / methanol / 1 h / 20 °C

5.1: 64 percent / diethyl azadicarboxylate (DEAD); PPh₃ / tetrahydrofuran / 16 h / 20 °C

With dmap; dichloro bis(acetonitrile) palladium(II); potassium tert-butylate; sec.-butyllithium; potassium carbonate; triethylamine; triphenylphosphine; p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1021/jm010256v

upstream raw materials:

3-N-benzoyluracil

(1R,2R,3S)-2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-ol

tert-butyl methyl ether

(3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one

Downstream raw materials:

(1'S,2'R,3'S)-1-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]cytosine

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