(2S,3S,4S)-2,3-Dimethyl-2-(3-oxo-butyl)-4-(tetrahydro-pyran-2-yloxy)-cyclohexanone

Base Information

• Chemical Name: (2S,3S,4S)-2,3-Dimethyl-2-(3-oxo-butyl)-4-(tetrahydro-pyran-2-yloxy)-cyclohexanone
• CAS No.: 111210-58-3
• Molecular Formula: C₁₇H₂₈O₄
• Molecular Weight: 296.407
• Mol file: 111210-58-3.mol

Synonyms:

Chemical Property of (2S,3S,4S)-2,3-Dimethyl-2-(3-oxo-butyl)-4-(tetrahydro-pyran-2-yloxy)-cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-2,3-Dimethyl-2-(3-oxo-butyl)-4-(tetrahydro-pyran-2-yloxy)-cyclohexanone

There total 17 articles about (2S,3S,4S)-2,3-Dimethyl-2-(3-oxo-butyl)-4-(tetrahydro-pyran-2-yloxy)-cyclohexanone 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:

2,3-dimethyl-1,4-dihydroxybenzene (608-43-5) → (2S,3S,4S)-2,3-Dimethyl-2-(3-oxo-butyl)-4-(tetrahydro-pyran-2-yloxy)-cyclohexanone (111210-58-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 99 percent / H₂ / Raney nickel (W-7) / methanol / 4 h / 130 °C / 95616.1 Torr

2: 8N Jones chromic acid reagent / acetone / 1 h / Ambient temperature

3: p-toluenesulfonic acid monohydrate / benzene / 20 h / Heating; azeotropic removal of water

4: p-toluenesulfonic acid monohydrate, H₂O / acetone / 2 h / Heating

5: 86 percent / Na, isopropyl alcohol / toluene / 1 h / Heating

6: 85 percent / 0.5N HCl / tetrahydrofuran / 1 h / Heating

7: 97 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 20 h / Ambient temperature

8: 60 percent NaH (mineraloil) / benzene / 20 h / Ambient temperature

9: 1.)p-toluenesulfonyl chloride, pyridine / 1.) 0 deg C, 3 h, 2.) 0 deg C, 20 h

10: 1.) potassium tert-butoxide / 1.) t-BuOH, room temp., 1 h, 2.) 30 min.

11: 20percent aq. KOH / bis-(2-hydroxy-ethyl) ether / 15 h / Heating

12: acetic anhydride, CH₃CO₂Na / 1.5 h / Heating

13: diethyl ether / 1.5 h / -25 °C

With pyridine; hydrogenchloride; potassium hydroxide; potassium tert-butylate; water; hydrogen; sodium acetate; sodium; pyridinium p-toluenesulfonate; acetic anhydride; chromic acid; sodium hydride; toluene-4-sulfonic acid; p-toluenesulfonyl chloride; isopropyl alcohol; Raney nickel (W-7); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene; diethylene glycol; benzene;

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → (2S,3S,4S)-2,3-Dimethyl-2-(3-oxo-butyl)-4-(tetrahydro-pyran-2-yloxy)-cyclohexanone (111210-58-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 20 h / Ambient temperature

2: 60 percent NaH (mineraloil) / benzene / 20 h / Ambient temperature

3: 1.)p-toluenesulfonyl chloride, pyridine / 1.) 0 deg C, 3 h, 2.) 0 deg C, 20 h

4: 1.) potassium tert-butoxide / 1.) t-BuOH, room temp., 1 h, 2.) 30 min.

5: 20percent aq. KOH / bis-(2-hydroxy-ethyl) ether / 15 h / Heating

6: acetic anhydride, CH₃CO₂Na / 1.5 h / Heating

7: diethyl ether / 1.5 h / -25 °C

With pyridine; potassium hydroxide; potassium tert-butylate; sodium acetate; pyridinium p-toluenesulfonate; acetic anhydride; sodium hydride; p-toluenesulfonyl chloride; In diethyl ether; dichloromethane; diethylene glycol; benzene;

Reference yield:

2-methylcyclohexane-1,3-dione (1193-55-1) → (2S,3S,4S)-2,3-Dimethyl-2-(3-oxo-butyl)-4-(tetrahydro-pyran-2-yloxy)-cyclohexanone (111210-58-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 68 percent / TosOH

2: 68 percent

4: 85 percent / 0.5N HCl / tetrahydrofuran / 1 h / Heating

5: 97 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 20 h / Ambient temperature

6: 60 percent NaH (mineraloil) / benzene / 20 h / Ambient temperature

7: 1.)p-toluenesulfonyl chloride, pyridine / 1.) 0 deg C, 3 h, 2.) 0 deg C, 20 h

8: 1.) potassium tert-butoxide / 1.) t-BuOH, room temp., 1 h, 2.) 30 min.

9: 20percent aq. KOH / bis-(2-hydroxy-ethyl) ether / 15 h / Heating

10: acetic anhydride, CH₃CO₂Na / 1.5 h / Heating

11: diethyl ether / 1.5 h / -25 °C

With pyridine; hydrogenchloride; potassium hydroxide; potassium tert-butylate; sodium acetate; pyridinium p-toluenesulfonate; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; p-toluenesulfonyl chloride; In tetrahydrofuran; diethyl ether; dichloromethane; diethylene glycol; benzene;

upstream raw materials:

methyllithium

(4aR*,5R*,6R*)-4a,5,6,7-tetrahydro-4a,5-dimethyl-6-(tetrahydropyran-2-yloxy)-2-chromanone

3,4-dihydro-2H-pyran

2-methylcyclohexane-1,3-dione

Downstream raw materials:

(3S,4R,4aR,5R,6R)-sporogen-AO 1

Refernces