4-(5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl)-4-(S)-methoxymethoxy-1-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-yn-1-(R)-ol

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Chemical Name:4-(5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl)-4-(S)-methoxymethoxy-1-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-yn-1-(R)-ol
CAS No.:790698-08-7
Molecular Formula:C₃₇H₅₈O₈
Molecular Weight:630.863
Hs Code.:

Synonyms:4-(5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl)-4-(S)-methoxymethoxy-1-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-yn-1-(R)-ol

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Chemical Property of 4-(5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl)-4-(S)-methoxymethoxy-1-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-yn-1-(R)-ol

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Technology Process of 4-(5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl)-4-(S)-methoxymethoxy-1-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-yn-1-(R)-ol

There total 20 articles about 4-(5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl)-4-(S)-methoxymethoxy-1-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-yn-1-(R)-ol 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: 70.0%

: 206260-14-2
5-(R)-[1-(R)-methoxymethoxy-tridecyl]tetrahydrofuran-2-(R)-carbaldehyde

: 790697-91-5
2-(S)-benzyloxymethyl-5-(S)-[1-(S)-methoxymethoxy-prop-2-ynyl]-2,5-dihydrofuran

: 790698-08-7
4-(5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl)-4-(S)-methoxymethoxy-1-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-yn-1-(R)-ol

Guidance literature:: 2-(S)-benzyloxymethyl-5-(S)-[1-(S)-methoxymethoxy-prop-2-ynyl]-2,5-dihydrofuran; With (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; 4 A molecular sieve; In toluene; at 20 ℃; for 0.5h;

5-(R)-[1-(R)-methoxymethoxy-tridecyl]tetrahydrofuran-2-(R)-carbaldehyde; In toluene;
DOI:10.1021/ja0455852

Reference yield:

: 109613-59-4
(S)-1-(benzyloxy)but-3-en-2-ol

: 790698-08-7
4-(5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl)-4-(S)-methoxymethoxy-1-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-yn-1-(R)-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 °C

1.2: 98 percent / tetrahydrofuran / 0 - 20 °C

2.1: Et₃N; pivaloyl chloride / diethyl ether / 1 h / 0 °C

2.2: 78 percent / n-BuLi / tetrahydrofuran; hexane; diethyl ether / 2 h / 0 °C

3.1: 91 percent / 4-(dimethylamino)-pyridine; DIEA / CH₂Cl₂ / 72 h / 20 °C

4.1: 92 percent / LiBH₄; MeOH / diethyl ether / 2 h / 0 °C

5.1: oxalyl chloride; dimethylsulfoxide; DIEA / CH₂Cl₂ / 0.25 h / -78 - 0 °C

6.1: t-BuOK / tetrahydrofuran; toluene / 1 h / 0 °C

6.2: 91 percent / tetrahydrofuran; toluene / 2 h / 20 °C

7.1: 99 percent / Cl₂(Cy₃P)(IMes)Ru=CHPh / CH₂Cl₂ / 8 h / Heating

8.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 6 h / 20 °C

9.1: Zn(OTf)2; (-)-N-methylephedrine; NEt₃ / 4A molecular sieves / toluene / 0.5 h / 20 °C

9.2: 70 percent / toluene

With methanol; dmap; lithium borohydride; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; oxalyl dichloride; (-)-N-methylephedrine; potassium tert-butylate; tetrabutyl ammonium fluoride; pivaloyl chloride; zinc trifluoromethanesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 6.1: Swern oxidation;
DOI:10.1021/ja0455852

Reference yield:

: 2930-05-4,14618-80-5,89616-40-0,16495-13-9
(S)-benzyl glycidyl ether

: 790698-08-7
4-(5-(S)-benzyloxymethyl-2,5-dihydrofuran-2-(S)-yl)-4-(S)-methoxymethoxy-1-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-yn-1-(R)-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 99 percent / n-BuLi / tetrahydrofuran / -10 - 25 °C

2.1: NaH / tetrahydrofuran / 1 h / 0 °C

2.2: 98 percent / tetrahydrofuran / 0 - 20 °C

3.1: Et₃N; pivaloyl chloride / diethyl ether / 1 h / 0 °C

3.2: 78 percent / n-BuLi / tetrahydrofuran; hexane; diethyl ether / 2 h / 0 °C

4.1: 91 percent / 4-(dimethylamino)-pyridine; DIEA / CH₂Cl₂ / 72 h / 20 °C

5.1: 92 percent / LiBH₄; MeOH / diethyl ether / 2 h / 0 °C

6.1: oxalyl chloride; dimethylsulfoxide; DIEA / CH₂Cl₂ / 0.25 h / -78 - 0 °C

7.1: t-BuOK / tetrahydrofuran; toluene / 1 h / 0 °C

7.2: 91 percent / tetrahydrofuran; toluene / 2 h / 20 °C

8.1: 99 percent / Cl₂(Cy₃P)(IMes)Ru=CHPh / CH₂Cl₂ / 8 h / Heating

9.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 6 h / 20 °C

10.1: Zn(OTf)2; (-)-N-methylephedrine; NEt₃ / 4A molecular sieves / toluene / 0.5 h / 20 °C

10.2: 70 percent / toluene

With methanol; dmap; lithium borohydride; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; n-butyllithium; oxalyl dichloride; (-)-N-methylephedrine; potassium tert-butylate; tetrabutyl ammonium fluoride; pivaloyl chloride; zinc trifluoromethanesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 7.1: Swern oxidation;
DOI:10.1021/ja0455852