(2Z,6E,13E)-3,8,8,14,18-Pentamethyl-11-methylenenonadeca-2,6,13,17-tetren-1-ol

Base Information

• Chemical Name: (2Z,6E,13E)-3,8,8,14,18-Pentamethyl-11-methylenenonadeca-2,6,13,17-tetren-1-ol
• CAS No.: 19953-93-6
• Molecular Formula: C25H42O
• Molecular Weight: 358.608
• Hs Code.: 2905290000
• Mol file: 19953-93-6.mol

Synonyms:3,7,11-trimethyldodeca-2(Z),6(E),10-trien-1-ol;(2-cis,6-trans)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol;(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylene-nonadeca-2,6,13,17-tetraen-1-ol;(Z,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol;2,6,10-Dodecatrien-1-ol,3,7,11-trimethyl-,(Z,E);

Chemical Property of (2Z,6E,13E)-3,8,8,14,18-Pentamethyl-11-methylenenonadeca-2,6,13,17-tetren-1-ol

Chemical Property:

• PSA: 20.23000
• LogP: 7.70680

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2Z,6E,13E)-3,8,8,14,18-Pentamethyl-11-methylenenonadeca-2,6,13,17-tetren-1-ol

There total 1 articles about (2Z,6E,13E)-3,8,8,14,18-Pentamethyl-11-methylenenonadeca-2,6,13,17-tetren-1-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:

1-chloro-3,7-dimethylocta-2,6-diene (5389-87-7) → (2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylenenonadeca-2,6,13,17-tetraen-1-ol (19953-93-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / 1.5M-n-BuLi / hexane; tetrahydrofuran

2: 1.) lithium di-isopropylamide, 2.) hexamethylphosphoric triamide, 3.) n-Bu₄NF*3H₂O

3: 94 percent / lithium, liquid NH₃ / diethyl ether / 0.5 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; tetrabutyl ammonium fluoride; ammonia; lithium; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1039/P19830001777

Reference yield:

(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylene-nonadeca-2,6,13,17-tetraen-1-ol (19953-93-6,23192-58-7,73454-66-7,145012-66-4) → 1,4-Pentanediol (626-95-9)

Guidance literature:

Multistep reaction; (i) O₃, CH₂Cl₂, (ii) NaBH₄, H₂O;

Reference yield:

(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylenenonadeca-2,6,13,17-tetraen-1-ol (19953-93-6) → 3-(3,4-dimethoxy-benzyloxy)-2-(3,8,8,14,18-pentamethyl-11-methylene-nonadeca-2,6,13,17-tetraenyloxy)-propionaldehyde

Guidance literature:

Multi-step reaction with 4 steps

1.1: phosphorus tribromide / diethyl ether / 1 h / 0 °C

2.1: sodium hydride / tetrahydrofuran; dimethylformamide / 0.5 h / 0 °C

2.2: 66 percent / tetrahydrofuran; dimethylformamide / 12 h / 20 °C

3.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

4.1: Dess-Martin periodinane; sodium bicarbonate / CH₂Cl₂ / 1.5 h / 0 °C

With tetrabutyl ammonium fluoride; phosphorus tribromide; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja065905c

upstream raw materials:

1-chloro-3,7-dimethylocta-2,6-diene

Downstream raw materials:

1,4-Pentanediol

4'-Nitroazobenzol-4-carbonsaeuremoencinylester

(S)-3-(3,4-dimethoxybenzyloxy)-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylenenonadeca-2,6,13,17-tertaen-1-yloxy]-1-propanol

methyl (R)-3-(3,4-dimethoxybenzyloxy)-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylenenonadeca-2,6,13,17-tertaen-1-yloxy]propanoate

Refernces

Cobalt-catalysed hydrovinylation as the key step in a short synthesis of moenocinol

10.1039/b822023a

The research focuses on the development of an efficient and atom-economic synthesis of moenocinol, the aglycone of moenomycin A, using a cobalt-catalysed 1,4-hydrovinylation reaction as the key step. The purpose of this study was to create a straightforward and convergent synthesis of moenocinol, which is a complex molecule with potential pharmaceutical applications. The researchers achieved this by utilizing a cobalt(I)-catalysed 1,4-hydrovinylation reaction that is both regio- and chemoselective, allowing for the formation of 1,4-diene subunits with high yield and excellent regioselectivity. The study concluded that this cobalt-catalysed approach offers the shortest route to moenocinol to date, with a total of five steps in the longest linear sequence starting from 5 and in seven total steps, marking a significant advancement in the synthesis of complex natural product-like structures.

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