3-[(1S,2S,3S)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid

Base Information

• Chemical Name: 3-[(1S,2S,3S)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid
• CAS No.: 111210-56-1
• Molecular Formula: C₁₆H₂₆O₅
• Molecular Weight: 298.379
• Mol file: 111210-56-1.mol

Synonyms:

Chemical Property of 3-[(1S,2S,3S)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(1S,2S,3S)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid

There total 15 articles about 3-[(1S,2S,3S)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid 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) → 3-[(1S,2S,3S)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid (111210-56-1)

Guidance literature:

Multi-step reaction with 11 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

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

Reference yield:

(2R*,3R*,4R*)-6-<(benzylthio)methylene>-2-<2-(ethoxycarbonyl)ethyl>-2,3-dimethyl-4-(tetrahydropyran-2-yloxy)cyclohexanone (111210-55-0) → 3-[(1S,2S,3S)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid (111210-56-1)

Guidance literature:

With potassium hydroxide; In diethylene glycol; for 15h; Yield given; Heating;

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → 3-[(1S,2S,3S)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid (111210-56-1)

Guidance literature:

Multi-step reaction with 5 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

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

upstream raw materials:

(2R*,3R*,4R*)-6-<(benzylthio)methylene>-2-<2-(ethoxycarbonyl)ethyl>-2,3-dimethyl-4-(tetrahydropyran-2-yloxy)cyclohexanone

3,4-dihydro-2H-pyran

2-methylcyclohexane-1,3-dione

2,3-dimethylcyclohex-2-en-1-one

Downstream raw materials:

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

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

Refernces