(5S)-3-[(R)-13-hydroxy-13-((R)-5-oxotetrahydrofuran-2-yl)tridecyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one

Base Information

Chemical Name:(5S)-3-[(R)-13-hydroxy-13-((R)-5-oxotetrahydrofuran-2-yl)tridecyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one
CAS No.:866885-85-0
Molecular Formula:C₂₈H₄₂O₅S
Molecular Weight:490.704
Hs Code.:

Synonyms:(5S)-3-[(R)-13-hydroxy-13-((R)-5-oxotetrahydrofuran-2-yl)tridecyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one

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Chemical Property of (5S)-3-[(R)-13-hydroxy-13-((R)-5-oxotetrahydrofuran-2-yl)tridecyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one

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Technology Process of (5S)-3-[(R)-13-hydroxy-13-((R)-5-oxotetrahydrofuran-2-yl)tridecyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one

There total 13 articles about (5S)-3-[(R)-13-hydroxy-13-((R)-5-oxotetrahydrofuran-2-yl)tridecyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-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: 86.0%

: 866885-81-6
(5S)-3-[(R)-13-hydroxy-13-((R)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one

: 866885-85-0
(5S)-3-[(R)-13-hydroxy-13-((R)-5-oxotetrahydrofuran-2-yl)tridecyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one

Guidance literature:: With hydrogen; Wilkinson's catalyst; In methanol; benzene; at 20 ℃; for 24h; under 760 Torr;
DOI:10.1016/j.bmc.2005.05.050

Reference yield:

: (5R)-[(1R)-benzyloxy-13-[(5S)-methyl-2-oxo-3-phenylsulfanyltetrahydrofuran-3-yl]-tridec-2-enyl]-5H-furan-2-one

: 866885-85-0
(5S)-3-[(R)-13-hydroxy-13-((R)-5-oxotetrahydrofuran-2-yl)tridecyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; for 24h; under 760.051 Torr;
DOI:10.1016/j.tet.2007.03.151

Reference yield:

: 69-65-8
mannitol

: 866885-85-0
(5S)-3-[(R)-13-hydroxy-13-((R)-5-oxotetrahydrofuran-2-yl)tridecyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: AcBr; Ac₂O; pyridine

1.2: Zn; NaOAc / acetic acid

1.3: NaOMe / methanol

2.1: 88 percent / dibutyltin oxide; tetrabutylammonium iodide / benzene / 18 h / Heating

3.1: 83 percent / i-Pr₂NEt / CH₂Cl₂ / 4 h / 20 °C

4.1: 66 percent / Hoveyda-Grubbs' first-generation catalyst / benzene / 80 °C

5.1: H₂ / Pd/C / ethyl acetate / 24 h / 760.05 Torr

With pyridine; Acetyl bromide; hydrogen; acetic anhydride; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; benzene;
DOI:10.1016/j.tet.2007.03.151