2-(S)-benzyloxymethyl-5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-ynyl}-2,5-dihydrofuran

Base Information

• Chemical Name: 2-(S)-benzyloxymethyl-5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-ynyl}-2,5-dihydrofuran
• CAS No.: 790698-09-8
• Molecular Formula: C₃₉H₆₂O₉
• Molecular Weight: 674.916

Synonyms:2-(S)-benzyloxymethyl-5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-ynyl}-2,5-dihydrofuran

Chemical Property of 2-(S)-benzyloxymethyl-5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-ynyl}-2,5-dihydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of 2-(S)-benzyloxymethyl-5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-ynyl}-2,5-dihydrofuran

There total 21 articles about 2-(S)-benzyloxymethyl-5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-ynyl}-2,5-dihydrofuran 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:

(S)-1-(benzyloxy)but-3-en-2-ol (109613-59-4) → 2-(S)-benzyloxymethyl-5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-ynyl}-2,5-dihydrofuran (790698-09-8)

Guidance literature:

Multi-step reaction with 11 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

10.1: 97 percent / 4-(dimethylamino)pyridine; DIEA / CH₂Cl₂ / 72 h / 20 °C

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:

(S)-benzyl glycidyl ether (2930-05-4,14618-80-5,89616-40-0,16495-13-9) → 2-(S)-benzyloxymethyl-5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-ynyl}-2,5-dihydrofuran (790698-09-8)

Guidance literature:

Multi-step reaction with 12 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

11.1: 97 percent / 4-(dimethylamino)pyridine; DIEA / CH₂Cl₂ / 72 h / 20 °C

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

Reference yield:

5-(R)-[1-(R)-methoxymethoxy-tridecyl]tetrahydrofuran-2-(R)-carbaldehyde (206260-14-2) → 2-(S)-benzyloxymethyl-5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]but-2-ynyl}-2,5-dihydrofuran (790698-09-8)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 70 percent / toluene

2.1: 97 percent / 4-(dimethylamino)pyridine; DIEA / CH₂Cl₂ / 72 h / 20 °C

With dmap; (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; 4 A molecular sieve; In dichloromethane; toluene;

DOI:10.1021/ja0455852

upstream raw materials:

(S)-1-(benzyloxy)but-3-en-2-ol

(S)-benzyl glycidyl ether

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

(1'R,2R,5R)-5-(hydroxymethyl)-2-<(1'-methoxymethoxy)tridecyl>tetrahydrofuran

Downstream raw materials:

(+)-gigantecin

3-[7-(5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]butyl}tetrahydrofuran-2-(S)-yl)-2-(R)-(4-methoxybenzyloxy)hept-3-en-5-ynyl]-5-(S)-methyl-5H-furan-2-one

(S)-3-[(R)-7-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-2-(4-methoxy-benzyloxy)-heptyl]-5-methyl-5H-furan-2-one

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