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

Base Information

• Chemical Name: 3-[(1R,2R,3S)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid methyl ester
• CAS No.: 122052-43-1
• Molecular Formula: C₁₇H₂₈O₅
• Molecular Weight: 312.406
• Mol file: 122052-43-1.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about 3-[(1R,2R,3S)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid methyl ester 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:

3,4-dihydro-2H-pyran (110-87-2) → 3-[(1R,2R,3S)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid methyl ester (122052-43-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / p-TsOH / CH₂Cl₂ / Ambient temperature

2: 60percent NaH / tetrahydrofuran / 1 h / Ambient temperature

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

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

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

6: 25percent aq. KOH / bis-(2-hydroxy-ethyl) ether / 24 h / Heating

With potassium hydroxide; potassium tert-butylate; sodium hydride; p-toluenesulfonyl chloride; lithium diisopropyl amide; toluene-4-sulfonic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; tert-butyl alcohol; diethylene glycol;

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

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,3S)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid methyl ester (122052-43-1)

Guidance literature:

Multi-step reaction with 14 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

With potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; baker's yeast; Amberlite IR-120; potassium tert-butylate; sodium hydride; p-toluenesulfonyl chloride; lithium diisopropyl amide; Sucrose; dmap; 2,2'-azobis(isobutyronitrile); toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; 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,3S)-1,2-Dimethyl-6-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-propionic acid methyl ester (122052-43-1)

Guidance literature:

Multi-step reaction with 11 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

With potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; Amberlite IR-120; potassium tert-butylate; sodium hydride; p-toluenesulfonyl chloride; lithium diisopropyl amide; 2,2'-azobis(isobutyronitrile); toluene-4-sulfonic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; tert-butyl alcohol; diethylene glycol; benzene;

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

upstream raw materials:

(1'R,2'R,3'S)-3-(1',2'-dimethyl-6'-oxo-3'-tetrahydropyranyloxycyclohexane)propanoic acid

3,4-dihydro-2H-pyran

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

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

Refernces