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

Base Information

• Chemical Name: 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
• CAS No.: 790698-11-2
• Molecular Formula: C₅₁H₈₀O₁₂
• Molecular Weight: 885.189
• Mol file: 790698-11-2.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 33 articles about 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 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: 64.0%

3-[4-iodo-2-(4-methoxy-benzyloxy)but-3-enyl]-5-methyl-5H-furan-2-one (790697-89-1) + 3-(5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]butyl}tetrahydrofuran-2-(S)-yl)prop-1-yne (790697-90-4) → 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 (790698-11-2)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1021/ja0455852

Reference yield:

5-(R)-[1-(R)-methoxymethoxy-tridecyl]tetrahydrofuran-2-(R)-carbaldehyde (206260-14-2) → 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 (790698-11-2)

Guidance literature:

Multi-step reaction with 6 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

3.1: 97 percent / H₂ / Pd/C / ethanol / 36 h

4.1: 0.062 g / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

5.2: HMPA / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.3: 95 percent / tetrahydrofuran; hexane / 1 h

6.1: 64 percent / Pd(PPh₃)4; CuI; DIEA / tetrahydrofuran / 4 h / 20 °C

With 2,6-dimethylpyridine; dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; (-)-N-methylephedrine; hydrogen; zinc trifluoromethanesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene;

DOI:10.1021/ja0455852

Reference yield:

(1'R,2R,5R)-5-(hydroxymethyl)-2-<(1'-methoxymethoxy)tridecyl>tetrahydrofuran (227186-05-2) → 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 (790698-11-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 0.42 g / oxalyl chloride; dimethylsulfoxide; DIEA / CH₂Cl₂ / -78 - 0 °C

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

2.2: 70 percent / toluene

3.1: 97 percent / 4-(dimethylamino)pyridine; DIEA / CH₂Cl₂ / 72 h / 20 °C

4.1: 97 percent / H₂ / Pd/C / ethanol / 36 h

5.1: 0.062 g / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

6.2: HMPA / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.3: 95 percent / tetrahydrofuran; hexane / 1 h

7.1: 64 percent / Pd(PPh₃)4; CuI; DIEA / tetrahydrofuran / 4 h / 20 °C

With 2,6-dimethylpyridine; dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; oxalyl dichloride; (-)-N-methylephedrine; hydrogen; zinc trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; 1.1: Swern oxidation;

DOI:10.1021/ja0455852

upstream raw materials:

3-[4-iodo-2-(4-methoxy-benzyloxy)but-3-enyl]-5-methyl-5H-furan-2-one

3-(5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]butyl}tetrahydrofuran-2-(S)-yl)prop-1-yne

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

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

Downstream raw materials:

(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

(+)-gigantecin