(1'''S,2''R,3RS,5S,5''S,13'R)-3-{13'-methoxymethoxy-13-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofuran-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulphanyl)tetrahydrofuran-2-one

Base Information

Chemical Name:(1'''S,2''R,3RS,5S,5''S,13'R)-3-{13'-methoxymethoxy-13-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofuran-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulphanyl)tetrahydrofuran-2-one
CAS No.:416843-12-4
Molecular Formula:C₄₅H₇₂O₇S
Molecular Weight:757.128
Hs Code.:

(1'''S,2''R,3RS,5S,5''S,13'R)-3-{13'-methoxymethoxy-13-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofuran-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulphanyl)tetrahydrofuran-2-one

Synonyms:(1'''S,2''R,3RS,5S,5''S,13'R)-3-{13'-methoxymethoxy-13-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofuran-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulphanyl)tetrahydrofuran-2-one

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Chemical Property of (1'''S,2''R,3RS,5S,5''S,13'R)-3-{13'-methoxymethoxy-13-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofuran-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulphanyl)tetrahydrofuran-2-one

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Technology Process of (1'''S,2''R,3RS,5S,5''S,13'R)-3-{13'-methoxymethoxy-13-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofuran-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulphanyl)tetrahydrofuran-2-one

There total 5 articles about (1'''S,2''R,3RS,5S,5''S,13'R)-3-{13'-methoxymethoxy-13-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofuran-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulphanyl)tetrahydrofuran-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: 74.0%

: (E,Z,3RS,5S)-3-(8'-iodooct-7'-enyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

: 416843-10-2
(2R,5S,1'R,1''S)-2-(1'-methoxymethoxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran

: 416843-12-4
(1'''S,2''R,3RS,5S,5''S,13'R)-3-{13'-methoxymethoxy-13-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofuran-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulphanyl)tetrahydrofuran-2-one

Guidance literature:: (E,Z,3RS,5S)-3-(8'-iodooct-7'-enyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one; With triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 1 ℃;

(2R,5S,1'R,1''S)-2-(1'-methoxymethoxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran; With copper(l) iodide; In tetrahydrofuran; for 8h; Further stages.;
DOI:10.1021/ol0102803

Reference yield:

: (2R,5S,1'R,1''S)-2-(1'-methoxymethoxy-4'-pentynyl)-5-(1''-hydroxytridecyl)tetrahydrofuran

: 416843-12-4
(1'''S,2''R,3RS,5S,5''S,13'R)-3-{13'-methoxymethoxy-13-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofuran-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulphanyl)tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 94 percent / (i-Pr)2NEt / CH₂Cl₂ / 24 h / 20 °C

2.1: Et₃N / Cl₂Pd(PPh₃)2 / tetrahydrofuran / 1 °C

2.2: 74 percent / CuI / tetrahydrofuran / 8 h

With triethylamine; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; dichloromethane; 2.1: Sonogashira cross coupling reaction;
DOI:10.1021/ol0102803

Reference yield:

: (Z,9S,10S)-10-(methoxymethoxy)docos-5-en-1-yn-9-ol

: 416843-12-4
(1'''S,2''R,3RS,5S,5''S,13'R)-3-{13'-methoxymethoxy-13-[5''-(1'''-methoxymethoxytridecyl)tetrahydrofuran-2''-yl]tridec-7'-en-9'-ynyl}-5-methyl-3-(phenylsulphanyl)tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 75 percent / t-BuOOH; 4 Angstroem molecular sieves / VO(acac)2 / 1,2-dichloro-ethane; toluene / 12 h / 23 °C

2.1: 72 percent / pyridine / 5 h / 20 °C

3.1: 92 percent / NaOH / methanol / 5 h

4.1: 94 percent / (i-Pr)2NEt / CH₂Cl₂ / 24 h / 20 °C

5.1: Et₃N / Cl₂Pd(PPh₃)2 / tetrahydrofuran / 1 °C

5.2: 74 percent / CuI / tetrahydrofuran / 8 h

With pyridine; tert.-butylhydroperoxide; sodium hydroxide; 4 A molecular sieve; triethylamine; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; toluene; 5.1: Sonogashira cross coupling reaction;
DOI:10.1021/ol0102803