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

Base Information

• Chemical Name: (2R/S,9R/S)-9-dihydro-5-(4-methoxybenzyloxy)narbonolide
• CAS No.: 918961-70-3
• Molecular Formula: C₂₈H₄₂O₆
• Molecular Weight: 474.638
• Mol file: 918961-70-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (2R/S,9R/S)-9-dihydro-5-(4-methoxybenzyloxy)narbonolide 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:

(2R/S,3S,4S,5S,6S,8R)-((3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl) 3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-oxononanoate (918961-69-0) → (2R/S,9R/S)-9-dihydro-5-(4-methoxybenzyloxy)narbonolide (918961-70-3)

Guidance literature:

With chromium dichloride; nickel dichloride; In dimethyl sulfoxide; at 20 ℃; for 12h;

DOI:10.1021/jo062047u

Reference yield:

(2S,4R)-2,4-Dimethyl-5-triisopropylsilanyloxy-pentanal → (2R/S,9R/S)-9-dihydro-5-(4-methoxybenzyloxy)narbonolide (918961-70-3)

Guidance literature:

Multi-step reaction with 11 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

With 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;

DOI:10.1021/jo062047u

Reference yield:

(2S,3S,4S,6R)-2,4,6-trimethyl-7-(triisopropylsilyloxy)heptane-1,3-diol (918961-61-2) → (2R/S,9R/S)-9-dihydro-5-(4-methoxybenzyloxy)narbonolide (918961-70-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 92 percent / CSA / CH₂Cl₂ / 12 h / 20 °C

2.1: 94 percent / DIBAL-H / toluene / 1 h / 0 °C

3.1: 86 percent / (COCl)2; DMSO; i-Pr₂NEt / CH₂Cl₂ / -78 - 0 °C

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

4.2: 76 percent / CH₂Cl₂ / 4 h / -78 - -20 °C

5.1: 82 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 0 - 20 °C

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

6.2: 61 percent / DMAP / benzene / 24 h / 20 °C

7.1: 79 percent / HF / pyridine; tetrahydrofuran / 48 h / 20 °C

8.1: 77 percent / Dess-Martin periodinane / CH₂Cl₂; pyridine / 12 h / 20 °C

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

With chromium dichloride; lithium hydroxide; 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; dichloromethane; water; dimethyl sulfoxide; toluene; 3.1: Swern Oxidation / 4.2: Evans Aldol Reaction / 8.1: Dess-Martin Oxidation / 9.1: Nozaki-Hiyama-Kishi Reaction;

DOI:10.1021/jo062047u

upstream raw materials:

(2R/S,3S,4S,5S,6S,8R)-((3R,4R,5E)-6-iodo-4-methylhex-5-en-3-yl) 3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-oxononanoate

(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

(R)-3-((3S,4S,6R)-3-hydroxy-2,4,6-trimethyl-7-(triisopropylsilyloxy)heptanoyl)-4-benzyloxazolin-2-one

Downstream raw materials:

(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