<4aβ,7aβ(E)>-(+/-)-7a-(4,8-Dimethyl-3,7-nonadienyl)hexahydro-4-<3-(phenylmethoxy)propyl>cyclopentapyran-3(1H)-one

Base Information

• Chemical Name: <4aβ,7aβ(E)>-(+/-)-7a-(4,8-Dimethyl-3,7-nonadienyl)hexahydro-4-<3-(phenylmethoxy)propyl>cyclopentapyran-3(1H)-one
• CAS No.: 117959-73-6
• Molecular Formula: C₂₉H₄₂O₃
• Molecular Weight: 438.651
• Mol file: 117959-73-6.mol

Synonyms:

Chemical Property of <4aβ,7aβ(E)>-(+/-)-7a-(4,8-Dimethyl-3,7-nonadienyl)hexahydro-4-<3-(phenylmethoxy)propyl>cyclopentapyran-3(1H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <4aβ,7aβ(E)>-(+/-)-7a-(4,8-Dimethyl-3,7-nonadienyl)hexahydro-4-<3-(phenylmethoxy)propyl>cyclopentapyran-3(1H)-one

There total 15 articles about <4aβ,7aβ(E)>-(+/-)-7a-(4,8-Dimethyl-3,7-nonadienyl)hexahydro-4-<3-(phenylmethoxy)propyl>cyclopentapyran-3(1H)-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: 92.0%

<2S-<1*<1R*,2S*,2(E)>>,2α,5β>>-1-<2-<2-(4,8-Dimethyl-3,7-nonadienyl)-2-(hydroxymethyl)cyclopentyl>-1-oxo-5-(phenylmethoxy)pentyl>-2,5-dimethylpyrrolidine (129539-98-6) → 7a-(4,8-Dimethyl-3,7-nonadienyl)hexahydro-4-<3-(phenylmethoxy)propyl>cyclopentapyran-3(1H)-one (117959-73-6,118015-93-3,129645-65-4,138383-35-4,138604-13-4,138604-14-5)

Guidance literature:

With potassium hydroxide; In ethylene glycol; at 165 ℃; for 50h;

DOI:10.1021/jo00307a006

Reference yield:

5-Benzyloxy-1-pyrrolidin-1-yl-pentan-1-one (117959-71-4) → <4aβ,7aβ(E)>-(+/-)-7a-(4,8-Dimethyl-3,7-nonadienyl)hexahydro-4-<3-(phenylmethoxy)propyl>cyclopentapyran-3(1H)-one (117959-73-6,118015-93-3,129645-65-4,138383-35-4,138604-13-4,138604-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / LDA / tetrahydrofuran / -78 - -25 °C

2: 1.) DIBAL; 2.) NaOH / 2.) EtOH, H₂O, 95 deg C

With sodium hydroxide; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/ja00234a046

Reference yield:

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) → <4aβ,7aβ(E)>-(+/-)-7a-(4,8-Dimethyl-3,7-nonadienyl)hexahydro-4-<3-(phenylmethoxy)propyl>cyclopentapyran-3(1H)-one (117959-73-6,118015-93-3,129645-65-4,138383-35-4,138604-13-4,138604-14-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) KOH; 2.) N,N'-carbonyldiimidazole / 1.) toluene, reflux

2: 87 percent / LDA / tetrahydrofuran / -78 - -25 °C

3: 1.) DIBAL; 2.) NaOH / 2.) EtOH, H₂O, 95 deg C

With potassium hydroxide; sodium hydroxide; diisobutylaluminium hydride; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/ja00234a046

upstream raw materials:

<2S-<1*<1R^*,2S^*,2(E)>>,2α,5β>>-1-<2-<2-(4,8-Dimethyl-3,7-nonadienyl)-2-(hydroxymethyl)cyclopentyl>-1-oxo-5-(phenylmethoxy)pentyl>-2,5-dimethylpyrrolidine

5-(phenylmethoxy)pentanoic acid chloride

(2S-trans)-2,5-Dimethyl-1-<1-oxo-5-(phenylmethoxy)-pentyl>pyrrolidine

Methyl <2S-<1*<1R^*,1(E),2S^*>>,2α,5β>>-1-(4,8-Dimethyl-3,7-nonadienyl)-2-<1-<(2,5-dimethyl-1-pyrrolidinyl)carbonyl>-4-(phenylmethoxy)butyl>cyclopentanecarboxylate

Downstream raw materials:

5-Benzyloxy-2-[(1S,2R)-2-((E)-4,8-dimethyl-nona-3,7-dienyl)-2-hydroxymethyl-cyclopentyl]-pentan-1-ol

<1α(R^*S^*),2α,2(E)>-(+/-)-2-(4,8-Dimethyl-3,7-nonadienyl)-2-(hydroxymethyl)-β-<3-(phenylmethoxy)propyl>cyclopentaneethanol

<1α(R^*S^*),2α,2(E)>-(+/-)-2-(4,8-Dimethyl-3,7-nonadienyl)-2-(formyl)-α-<3-(phenylmethoxy)propyl>cyclopentaneacetaldehyde

(-)-Secodaphniphylline