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

Base Information

• Chemical Name: 3-[(1R,2R,3R)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid
• CAS No.: 122090-97-5
• Molecular Formula: C₁₆H₂₆O₅
• Molecular Weight: 298.379
• Mol file: 122090-97-5.mol

Synonyms:

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

There total 20 articles about 3-[(1R,2R,3R)-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:

ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate (14160-65-7,77793-24-9,122090-88-4) → 3-[(1R,2R,3R)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid (122090-97-5)

Guidance literature:

Multi-step reaction with 20 steps

1: 10 g / baker's yeast, sucrose / H₂O; ethanol / 30 °C

2: 4-N,N-dimethylaminopyridine / pyridine / Ambient temperature

3: 95 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

4: 87 percent / p-TsOH / CH₂Cl₂ / 3 h / Ambient temperature

5: 83 percent / NBS / AIBN / benzene / 1 h / 50 °C

6: 83 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

7: 99 percent / Amberlite IR-120 / H₂O / 3 h / Heating

8: 90 percent / p-TsOH / CH₂Cl₂ / Ambient temperature

9: 60percent NaH / tetrahydrofuran / 1 h / Ambient temperature

10: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 0 °C

11: 1.) p-TsCl / 1.) pyridine, 0 deg C, 3 h, 2.) pyridine, room temp.

12: t-BuOK / 2-methyl-propan-2-ol / 2 h / Ambient temperature

13: 25percent aq. KOH / bis-(2-hydroxy-ethyl) ether / 24 h / Heating

14: 2.) LiOH*H₂O / 1.) p-TsOH / 1.) benzene, 6 h, reflux, 2.) H₂O, MeOH, room temp.

15: NaHCO₃ / dimethylformamide / 60 °C

16: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 1.5 h, 2.) CH₂Cl₂, -70 -> 0 deg C

17: Li, EtOH / liquid ammonia; diethyl ether / 1.) -78 deg C, 1 h, 2.) -33 deg C, 1 h

18: 430 mg / p-TsOH / 3 h / Heating

19: pyridinium p-toluenesulfonate / CH₂Cl₂ / Ambient temperature

20: 500 mg / LiOH*H₂O / methanol; H₂O / Ambient temperature

With potassium hydroxide; lithium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; baker's yeast; oxalyl dichloride; Amberlite IR-120; ethanol; potassium tert-butylate; lithium; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; lithium diisopropyl amide; Sucrose; dmap; 2,2'-azobis(isobutyronitrile); pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ammonia; water; N,N-dimethyl-formamide; tert-butyl alcohol; diethylene glycol; benzene;

DOI:10.1016/S0040-4020(01)86136-6

Reference yield:

(1S,2S)-4,4-ethylenedioxy-2-hydroxymethylcyclohexanol (96894-00-7) → 3-[(1R,2R,3R)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid (122090-97-5)

Guidance literature:

Multi-step reaction with 17 steps

1: 87 percent / p-TsOH / CH₂Cl₂ / 3 h / Ambient temperature

2: 83 percent / NBS / AIBN / benzene / 1 h / 50 °C

3: 83 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

4: 99 percent / Amberlite IR-120 / H₂O / 3 h / Heating

5: 90 percent / p-TsOH / CH₂Cl₂ / Ambient temperature

6: 60percent NaH / tetrahydrofuran / 1 h / Ambient temperature

7: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 0 °C

8: 1.) p-TsCl / 1.) pyridine, 0 deg C, 3 h, 2.) pyridine, room temp.

9: t-BuOK / 2-methyl-propan-2-ol / 2 h / Ambient temperature

10: 25percent aq. KOH / bis-(2-hydroxy-ethyl) ether / 24 h / Heating

11: 2.) LiOH*H₂O / 1.) p-TsOH / 1.) benzene, 6 h, reflux, 2.) H₂O, MeOH, room temp.

12: NaHCO₃ / dimethylformamide / 60 °C

13: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 1.5 h, 2.) CH₂Cl₂, -70 -> 0 deg C

14: Li, EtOH / liquid ammonia; diethyl ether / 1.) -78 deg C, 1 h, 2.) -33 deg C, 1 h

15: 430 mg / p-TsOH / 3 h / Heating

16: pyridinium p-toluenesulfonate / CH₂Cl₂ / Ambient temperature

17: 500 mg / LiOH*H₂O / methanol; H₂O / Ambient temperature

With potassium hydroxide; lithium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; Amberlite IR-120; ethanol; potassium tert-butylate; lithium; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; lithium diisopropyl amide; 2,2'-azobis(isobutyronitrile); pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; ammonia; water; N,N-dimethyl-formamide; tert-butyl alcohol; diethylene glycol; benzene;

DOI:10.1016/S0040-4020(01)86136-6

Reference yield:

(1R,2S)-5,5-(Ethylendioxy)-2-hydroxycyclohexancarbonsaeure-ethylester (96893-99-1) → 3-[(1R,2R,3R)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid (122090-97-5)

Guidance literature:

Multi-step reaction with 19 steps

1: 4-N,N-dimethylaminopyridine / pyridine / Ambient temperature

2: 95 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

3: 87 percent / p-TsOH / CH₂Cl₂ / 3 h / Ambient temperature

4: 83 percent / NBS / AIBN / benzene / 1 h / 50 °C

5: 83 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

6: 99 percent / Amberlite IR-120 / H₂O / 3 h / Heating

7: 90 percent / p-TsOH / CH₂Cl₂ / Ambient temperature

8: 60percent NaH / tetrahydrofuran / 1 h / Ambient temperature

9: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 0 °C

10: 1.) p-TsCl / 1.) pyridine, 0 deg C, 3 h, 2.) pyridine, room temp.

11: t-BuOK / 2-methyl-propan-2-ol / 2 h / Ambient temperature

12: 25percent aq. KOH / bis-(2-hydroxy-ethyl) ether / 24 h / Heating

13: 2.) LiOH*H₂O / 1.) p-TsOH / 1.) benzene, 6 h, reflux, 2.) H₂O, MeOH, room temp.

14: NaHCO₃ / dimethylformamide / 60 °C

15: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 1.5 h, 2.) CH₂Cl₂, -70 -> 0 deg C

16: Li, EtOH / liquid ammonia; diethyl ether / 1.) -78 deg C, 1 h, 2.) -33 deg C, 1 h

17: 430 mg / p-TsOH / 3 h / Heating

18: pyridinium p-toluenesulfonate / CH₂Cl₂ / Ambient temperature

19: 500 mg / LiOH*H₂O / methanol; H₂O / Ambient temperature

With potassium hydroxide; lithium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; Amberlite IR-120; ethanol; potassium tert-butylate; lithium; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; lithium diisopropyl amide; dmap; 2,2'-azobis(isobutyronitrile); pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; ammonia; water; N,N-dimethyl-formamide; tert-butyl alcohol; diethylene glycol; benzene;

DOI:10.1016/S0040-4020(01)86136-6

upstream raw materials:

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

ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

(1S,2S)-4,4-ethylenedioxy-2-hydroxymethylcyclohexanol

(1R,2S)-5,5-(Ethylendioxy)-2-hydroxycyclohexancarbonsaeure-ethylester

Refernces