(E)-(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione

Base Information

• Chemical Name: (E)-(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione
• CAS No.: 918961-71-4
• Molecular Formula: C₂₈H₄₀O₆
• Molecular Weight: 472.622
• Mol file: 918961-71-4.mol

Synonyms:(E)-(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione

Chemical Property of (E)-(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione

There total 15 articles about (E)-(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione 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: 83.0%

C28H42O6 (1009036-60-5) → (E)-(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione (918961-71-4)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/jo702384d

Reference yield:

(2S,4R)-2,4-Dimethyl-5-triisopropylsilanyloxy-pentanal → (E)-(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione (918961-71-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 1 h / 0 °C

1.2: 78 percent / CH₂Cl₂ / 2.5 h / -78 - -10 °C

2.1: 88 percent / LiBH₄ / tetrahydrofuran; methanol / 0.75 h / 0 °C

3.1: 92 percent / CSA / CH₂Cl₂ / 12 h / 20 °C

4.1: 94 percent / DIBAL-H / toluene / 1 h / 0 °C

5.1: 86 percent / (COCl)2; DMSO; i-Pr₂NEt / CH₂Cl₂ / -78 - 0 °C

6.1: Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 1 h / 0 °C

6.2: 76 percent / CH₂Cl₂ / 4 h / -78 - -20 °C

7.1: 82 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 0 - 20 °C

8.1: Et₃N; 2,4,6-trichlorobenzoylchloride / tetrahydrofuran / 3 h / 20 °C

8.2: 61 percent / DMAP / benzene / 24 h / 20 °C

9.1: 79 percent / HF / pyridine; tetrahydrofuran / 48 h / 20 °C

10.1: 77 percent / Dess-Martin periodinane / CH₂Cl₂; pyridine / 12 h / 20 °C

11.1: CrCl₂; NiCl₂ / dimethylsulfoxide / 12 h / 20 °C

12.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 18 h / 20 °C

With pyridine; chromium dichloride; lithium hydroxide; lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; hydrogen fluoride; dihydrogen peroxide; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; 1.2: Evans Aldol Reaction / 5.1: Swern Oxidation / 6.2: Evans Aldol Reaction / 10.1: Dess-Martin Oxidation / 11.1: Nozaki-Hiyama-Kishi Reaction / 12.1: Dess-Martin Oxidation;

DOI:10.1021/jo062047u

Reference yield:

(2S,3S,4S,6R)-2,4,6-trimethyl-7-(triisopropylsilyloxy)heptane-1,3-diol (918961-61-2) → (E)-(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione (918961-71-4)

Guidance literature:

Multi-step reaction with 2 steps

1: MeLi / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

2: 31.2 mg / tetrahydrofuran; diethyl ether / -78 - 20 °C

With methyllithium; In tetrahydrofuran; diethyl ether; 1: Rearrangement / 2: Acylation;

DOI:10.1021/ja994209s

upstream raw materials:

(2R/S,9R/S)-9-dihydro-5-(4-methoxybenzyloxy)narbonolide

(3S,9R/S)-3,9-tetrahydro-5-(4-methoxybenzyloxy)narbonolide

(2S,3S,4S,6R)-2,4,6-trimethyl-7-(triisopropylsilyloxy)heptane-1,3-diol

(3S,4S,6R)-3-(4-methoxybenzyloxy)-2,4,6,-trimethyl-7-(triisopropylsilyloxy)heptanal

Downstream raw materials:

narbonolide