(4R^*,6S^*,7S^*)-7-acetyloxy-4,6-dimethyl-3-nonanone

Base Information

• Chemical Name: (4R^*,6S^*,7S^*)-7-acetyloxy-4,6-dimethyl-3-nonanone
• CAS No.: 72485-37-1
• Molecular Formula: C₁₃H₂₄O₃
• Molecular Weight: 228.332
• Mol file: 72485-37-1.mol

Synonyms:

Chemical Property of (4R^*,6S^*,7S^*)-7-acetyloxy-4,6-dimethyl-3-nonanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R^*,6S^*,7S^*)-7-acetyloxy-4,6-dimethyl-3-nonanone

There total 133 articles about (4R^*,6S^*,7S^*)-7-acetyloxy-4,6-dimethyl-3-nonanone 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: 80.0%

(4R,6S,7S)-7-(benzyloxy)-4,6-dimethylnonan-3-one (1360170-65-5) + acetic anhydride (108-24-7) → (4R,6S,7S)-7-acetoxy-4,6-dimethyl-3-nonanone (72485-37-1,78479-18-2,78479-19-3,78479-20-6,78479-21-7,82335-98-6,83997-86-8,86421-20-7,86562-39-2,93218-39-4,93218-41-8,93218-42-9,93218-47-4,84277-59-8)

Guidance literature:

(4R,6S,7S)-7-(benzyloxy)-4,6-dimethylnonan-3-one; With palladium 10% on activated carbon; hydrogen; In benzene; at 20 ℃; for 4h;

acetic anhydride; With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.11.013

Reference yield:

(2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether (86535-07-1) → (4R,6S,7S)-7-acetoxy-4,6-dimethyl-3-nonanone (72485-37-1,78479-18-2,78479-19-3,78479-20-6,78479-21-7,82335-98-6,83997-86-8,86421-20-7,86562-39-2,93218-39-4,93218-41-8,93218-42-9,93218-47-4,84277-59-8)

Guidance literature:

Multi-step reaction with 8 steps

1: p-TsOH / diethyl ether / Ambient temperature

2: H₂ / Pd-C (5percent) / ethanol

3: 2.) p-TsOH, dihydropyran / 1.) C₅H₅N, 8 h; 2.) ether, room temp.

4: K₂CO₃, NaI / acetone / 120 h / Ambient temperature

5: TsOH-C₅H₅N (PPTS) / Ambient temperature

6: LDA / diethyl ether / -115 - -20 °C

7: 2.) aq. HCl / 1.) 16 h, reflux; 2.) n-pentane, 35 min., room temp.

8: pyridine / Ambient temperature

With 3,4-dihydro-2H-pyran; hydrogenchloride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; toluene-4-sulfonic acid; sodium iodide; lithium diisopropyl amide; palladium on activated charcoal; In pyridine; diethyl ether; ethanol; acetone;

DOI:10.1016/0040-4020(82)80081-1

Reference yield:

D,L-threo-β-methylaspartic acid (642-92-2,1114-07-4,2955-50-2,4846-45-1,5941-19-5,6061-13-8,6667-60-3,7298-96-6,31571-69-4,86562-29-0,121570-10-3,127001-58-5) → (4R,6S,7S)-7-acetoxy-4,6-dimethyl-3-nonanone (72485-37-1,78479-18-2,78479-19-3,78479-20-6,78479-21-7,82335-98-6,83997-86-8,86421-20-7,86562-39-2,93218-39-4,93218-41-8,93218-42-9,93218-47-4,84277-59-8)

Guidance literature:

Multi-step reaction with 21 steps

1: 1.) acetone, MeOH, water; 2.) water, HCl, pH=3, EtOH

2: NaNO₂ / H₂O; H₂SO₄ / 0 - 25 °C

3: diethyl ether

4: p-TsOH / diethyl ether / Ambient temperature

5: LAH / diethyl ether

6: p-TsOH / methanol / Ambient temperature

7: p-TsOH / Ambient temperature

8: NaCH₂SOMe / dimethylsulfoxide / 5 h / Ambient temperature

9: aq. HCl; methanol; H₂O / 6.5 h / 60 °C

10: 92 percent / pyridine / 0 - 5 °C

11: 66 percent / KOH / methanol / 0.58 h / 0 - 17 °C

12: 82 percent / CuI / diethyl ether / -55 - -20 °C

13: 98 percent / p-TsOH / diethyl ether / Ambient temperature

14: 88 percent / H₂ / Pd-C (5percent) / ethanol

15: 2.) p-TsOH, dihydropyran / 1.) C₅H₅N, 8 h; 2.) ether, room temp.

16: K₂CO₃, NaI / acetone / 120 h / Ambient temperature

17: 98 percent / p-TsOH / methanol / Ambient temperature

18: TsOH-C₅H₅N (PPTS) / Ambient temperature

19: LDA / diethyl ether / -115 - -20 °C

20: 2.) aq. HCl / 1.) 16 h, reflux; 2.) n-pentane, 35 min., room temp.

21: pyridine / Ambient temperature

With 3,4-dihydro-2H-pyran; hydrogenchloride; potassium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; dimsylsodium; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; toluene-4-sulfonic acid; sodium iodide; lithium diisopropyl amide; sodium nitrite; palladium on activated charcoal; In pyridine; hydrogenchloride; methanol; diethyl ether; ethanol; sulfuric acid; water; dimethyl sulfoxide; acetone;

DOI:10.1016/0040-4020(82)80081-1

upstream raw materials:

acetic anhydride

(4RS,6S,7S)-Serricornin

3-methoxycarbonyltetrahydropyran-4-one

(2S,3S)-3-<(tertbutyl)dimethylsilyloxy>-2-methylpentan-1-ol

Downstream raw materials:

(4R^*,6S^*,7S^*)-7-acetyloxy-4,6-dimethyl-3-nonanone

(4R^*,6R^*,7R^*)-7-acetyloxy-4,6-dimethyl-3-nonanone

Refernces

• 1、 Lozanova,Stepanov,Veselovsky. "Synthesis of a biologically active analog of the sex pheromone of cigarette beetle (Lasioderma serricorne)". . p. 1254 - 1257. Retrieved 2007/10/03.
• 2、 Bhushan,Chandrasekaran. "A novel approach to the synthesis of (±)serricornin and (±)anhydroserricornin, the sex pheromone of the cigarette beetle". . p. 660 - 663. Retrieved 2007/10/02.