(3S,11S)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one

Base Information

• Chemical Name: (3S,11S)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one
• CAS No.: 79016-01-6
• Molecular Formula: C₃₈H₆₄O₂
• Molecular Weight: 552.925
• Mol file: 79016-01-6.mol

Synonyms:

Chemical Property of (3S,11S)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,11S)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one

There total 36 articles about (3S,11S)-29-benzyloxy-3,11-dimethylnonacos-14-yn-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:

(3R)-citronellol (1117-61-9) → (3S,11S)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one (79016-01-6)

Guidance literature:

Multi-step reaction with 18 steps

1: pyridine / 2 h / 0 - 5 °C

2: 85 percent / sodium iodide / acetone / 1.) reflux, 4 h; 2.) room temp., 14 h

3: 78 percent / NaOEt / ethanol / 1.) 0-5 deg C, 1 h; 2.) reflux, 4 h

4: 92 percent / KOH / aq. ethanol / 2.5 h / Heating

5: 92 percent / LAH / diethyl ether / 4 h / Ambient temperature

6: 96.5 percent / pyridine / 5 h / Ambient temperature

7: 90 percent / m-chloroperbenzoic acid / CHCl₃

8: 81 percent / HIO₄*2H₂O / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature

9: 1.) n-buLi / 1.) n-hexane, THF, -30 deg C; 2.) -50 to -10 deg C, THF, -10 deg C, 1 h

10: 85 percent / Br₂ / CH₂Cl₂ / 1 h

11: 69.4 percent / NaNH₂, 10 percent NaOH / methanol / 0.5 h / Heating

12: 5.85 g / p-TsOH / diethyl ether / Ambient temperature

13: 13.2 g / n-BuLI / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 1 h / Ambient temperature

14: 4.3 g / p-toluenesulfonic acid / methanol / 2 h / 40 - 50 °C

15: 5.32 g / pyridine / 2 h

16: 80 percent

17: 860 mg / hydration

18: 800 mg / Jones CrO₃ / acetone

With chromium(VI) oxide; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; bromine; sodium ethanolate; toluene-4-sulfonic acid; sodium amide; periodic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane; chloroform; acetone;

DOI:10.1016/S0040-4020(01)92448-2

Reference yield:

(R)-citronellic acid (18951-85-4,57030-77-0) → (3S,11S)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one (79016-01-6)

Guidance literature:

Multi-step reaction with 19 steps

1: 92 percent / LAH / diethyl ether / 3 h / Ambient temperature

2: pyridine / 2 h / 0 - 5 °C

3: 85 percent / sodium iodide / acetone / 1.) reflux, 4 h; 2.) room temp., 14 h

4: 78 percent / NaOEt / ethanol / 1.) 0-5 deg C, 1 h; 2.) reflux, 4 h

5: 92 percent / KOH / aq. ethanol / 2.5 h / Heating

6: 92 percent / LAH / diethyl ether / 4 h / Ambient temperature

7: 96.5 percent / pyridine / 5 h / Ambient temperature

8: 90 percent / m-chloroperbenzoic acid / CHCl₃

9: 81 percent / HIO₄*2H₂O / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature

10: 1.) n-buLi / 1.) n-hexane, THF, -30 deg C; 2.) -50 to -10 deg C, THF, -10 deg C, 1 h

11: 85 percent / Br₂ / CH₂Cl₂ / 1 h

12: 69.4 percent / NaNH₂, 10 percent NaOH / methanol / 0.5 h / Heating

13: 5.85 g / p-TsOH / diethyl ether / Ambient temperature

14: 13.2 g / n-BuLI / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 1 h / Ambient temperature

15: 4.3 g / p-toluenesulfonic acid / methanol / 2 h / 40 - 50 °C

16: 5.32 g / pyridine / 2 h

17: 80 percent

18: 860 mg / hydration

19: 800 mg / Jones CrO₃ / acetone

With chromium(VI) oxide; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; bromine; sodium ethanolate; toluene-4-sulfonic acid; sodium amide; periodic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane; chloroform; acetone;

DOI:10.1016/S0040-4020(01)92448-2

Reference yield:

(S)-(+)-8-acetoxy-4-methyloctanal (69274-74-4) → (3S,11S)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one (79016-01-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) n-buLi / 1.) n-hexane, THF, -30 deg C; 2.) -50 to -10 deg C, THF, -10 deg C, 1 h

2: 85 percent / Br₂ / CH₂Cl₂ / 1 h

3: 69.4 percent / NaNH₂, 10 percent NaOH / methanol / 0.5 h / Heating

4: 5.85 g / p-TsOH / diethyl ether / Ambient temperature

5: 13.2 g / n-BuLI / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 1 h / Ambient temperature

6: 4.3 g / p-toluenesulfonic acid / methanol / 2 h / 40 - 50 °C

7: 5.32 g / pyridine / 2 h

8: 80 percent

9: 860 mg / hydration

10: 800 mg / Jones CrO₃ / acetone

With chromium(VI) oxide; sodium hydroxide; n-butyllithium; bromine; toluene-4-sulfonic acid; sodium amide; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; acetone;

DOI:10.1016/S0040-4020(01)92448-2

upstream raw materials:

(3S,11S)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-ol

1,14-tetradecanediol

(3R)-citronellol

(R)-citronellic acid