ethyl 3-(5-((1S,2R)-7-(benzyloxy)-1,2-dihydroxyheptyl)furan-2-yl)propanoate

Base Information

• Chemical Name: ethyl 3-(5-((1S,2R)-7-(benzyloxy)-1,2-dihydroxyheptyl)furan-2-yl)propanoate
• CAS No.: 1618099-42-5
• Molecular Formula: C₂₃H₃₂O₆
• Molecular Weight: 404.503

Synonyms:ethyl 3-(5-((1S,2R)-7-(benzyloxy)-1,2-dihydroxyheptyl)furan-2-yl)propanoate

Chemical Property of ethyl 3-(5-((1S,2R)-7-(benzyloxy)-1,2-dihydroxyheptyl)furan-2-yl)propanoate

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Technology Process of ethyl 3-(5-((1S,2R)-7-(benzyloxy)-1,2-dihydroxyheptyl)furan-2-yl)propanoate

There total 1 articles about ethyl 3-(5-((1S,2R)-7-(benzyloxy)-1,2-dihydroxyheptyl)furan-2-yl)propanoate 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:

ethyl 3-(5-(7-(benzyloxy)hept-1-enyl)furan-2-yl)propanoate → ethyl 3-(5-((1S,2R)-7-(benzyloxy)-1,2-dihydroxyheptyl)furan-2-yl)propanoate (1618099-42-5) + ethyl 3-(5-(7-(benzyloxy)-1,2-dihydroxyheptyl)furan-2-yl)propanoate

Guidance literature:

With potassium osmate(VI) dihydrate; methanesulfonamide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; tert-butyl alcohol; at 0 ℃; for 96h; Overall yield = 84 %; Overall yield = 9.16 g; enantioselective reaction;

DOI:10.1021/jo501142q

Reference yield: 72.0%

ethyl 3-(5-((1S,2R)-7-(benzyloxy)-1,2-dihydroxyheptyl)furan-2-yl)propanoate (1618099-42-5) → ethyl 3-((7R)-7-(5-(benzyloxy)pentyl)-2-oxo-6,8-dioxabicyclo[3.2.1]oct-3-en-5-yl)propanoate

Guidance literature:

ethyl 3-(5-((1S,2R)-7-(benzyloxy)-1,2-dihydroxyheptyl)furan-2-yl)propanoate; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 2h;

With camphor-10-sulfonic acid; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1021/jo501142q

Reference yield:

ethyl 3-(5-((1S,2R)-7-(benzyloxy)-1,2-dihydroxyheptyl)furan-2-yl)propanoate (1618099-42-5) → C29H48O6Si

Guidance literature:

Multi-step reaction with 4 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C

1.2: 0.33 h / 0 °C

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2.17 h / 20 °C / 760.05 Torr / Inert atmosphere

3.1: potassium tri-sec-butyl-borohydride / tetrahydrofuran; toluene / 2 h / -78 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C

With 1H-imidazole; palladium 10% on activated carbon; hydrogen; potassium tri-sec-butyl-borohydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo501142q

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