Acetic acid (E)-3-methyl-5-((2R,3R)-3-methyl-3-phenylcarbamoyloxymethyl-oxiranyl)-pent-2-enyl ester

Base Information

Chemical Name:Acetic acid (E)-3-methyl-5-((2R,3R)-3-methyl-3-phenylcarbamoyloxymethyl-oxiranyl)-pent-2-enyl ester
CAS No.:90460-93-8
Molecular Formula:C₁₉H₂₅NO₅
Molecular Weight:347.411
Hs Code.:

Synonyms:Acetic acid (E)-3-methyl-5-((2R,3R)-3-methyl-3-phenylcarbamoyloxymethyl-oxiranyl)-pent-2-enyl ester

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Chemical Property of Acetic acid (E)-3-methyl-5-((2R,3R)-3-methyl-3-phenylcarbamoyloxymethyl-oxiranyl)-pent-2-enyl ester

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Technology Process of Acetic acid (E)-3-methyl-5-((2R,3R)-3-methyl-3-phenylcarbamoyloxymethyl-oxiranyl)-pent-2-enyl ester

There total 2 articles about Acetic acid (E)-3-methyl-5-((2R,3R)-3-methyl-3-phenylcarbamoyloxymethyl-oxiranyl)-pent-2-enyl ester 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: 94.7%

: 86561-75-3
(E)-5-((2R,3R)-3-(hydroxymethyl)-3-methyloxiran-2-yl)-3-methylpent-2-en-1-yl acetate

: 103-71-9
phenyl isocyanate

: 90460-93-8
Acetic acid (E)-3-methyl-5-((2R,3R)-3-methyl-3-phenylcarbamoyloxymethyl-oxiranyl)-pent-2-enyl ester

Guidance literature:: With triethylamine; In dichloromethane; for 24h; Ambient temperature;
DOI:10.1021/jo00188a014

Reference yield:

: Acetic acid (1E,3Z,5E)-7-hydroxy-2,6-dimethyl-hepta-1,3,5-trienyl ester

: 90460-93-8
Acetic acid (E)-3-methyl-5-((2R,3R)-3-methyl-3-phenylcarbamoyloxymethyl-oxiranyl)-pent-2-enyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 50 percent / 1.) Ti(O-i-Pr)4, (-)-Diethyl D-tartrate, t-BuOOH, / CH₂Cl₂ / -15 °C

2: 94.7 percent / Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; triethylamine; In dichloromethane;
DOI:10.1021/jo00188a014

Reference yield:

: 90460-93-8
Acetic acid (E)-3-methyl-5-((2R,3R)-3-methyl-3-phenylcarbamoyloxymethyl-oxiranyl)-pent-2-enyl ester

: 90481-26-8
Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2S,5R)-2-methyl-5-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / 5percent HClO₄ / acetonitrile / 4 h / Ambient temperature

2: 90 percent / Phosphorus oxychloride / CH₂Cl₂ / 24 h / Ambient temperature

3: 90 percent / K₂CO₃ / methanol / 1 h / 0 °C

4: 83 percent / Dowex H⁺ / methanol / 24 h / Ambient temperature

5: 60 percent / 1.) Ti(O-i-Pr), (-)-Diethyl D-tatrate, t-BuOOH, 2.) Tattratic acid / CH₂Cl₂ / 1.) -23 degC, 30 min. 2.) stirring

6: 82.5 percent / pyridine / 0 °C / overnight

With titanium(IV) isopropylate; tert.-butylhydroperoxide; perchloric acid; Dowex H⁺; Tattratic acid; potassium carbonate; (-)-diethyl tartrate; trichlorophosphate; In pyridine; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo00188a014