(2S,5R)-2-Hydroxy-2-methyl-5-((R)-1-methyl-allyl)-cyclohexane-1,4-dione

Base Information

• Chemical Name: (2S,5R)-2-Hydroxy-2-methyl-5-((R)-1-methyl-allyl)-cyclohexane-1,4-dione
• CAS No.: 139618-35-2
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.246
• Mol file: 139618-35-2.mol

Synonyms:(2S,5R)-2-Hydroxy-2-methyl-5-((R)-1-methyl-allyl)-cyclohexane-1,4-dione

Chemical Property of (2S,5R)-2-Hydroxy-2-methyl-5-((R)-1-methyl-allyl)-cyclohexane-1,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-2-Hydroxy-2-methyl-5-((R)-1-methyl-allyl)-cyclohexane-1,4-dione

There total 14 articles about (2S,5R)-2-Hydroxy-2-methyl-5-((R)-1-methyl-allyl)-cyclohexane-1,4-dione 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:

(1R,2R,4S,6S)-(-)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol (24120-79-4) → (2S,5R)-2-Hydroxy-2-methyl-5-((R)-1-methyl-allyl)-cyclohexane-1,4-dione (139618-35-2)

Guidance literature:

Multi-step reaction with 14 steps

1: NaBH₄ / ethanol

2: p-TsOH*2H₂O / acetone / Heating

3: mCPBA / CH₂Cl₂ / 0 °C

4: pyridine / benzene / Heating

5: 69 percent / diethylaluminum 2,2,6,6-tetramethylpiperidide / benzene / 0 °C

6: MnO₂ / CH₂Cl₂

7: NaClO₂, NaHPO₄, 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol

8: I₂, KI, sat. NaHCO₃

9: 80 percent / n-Bu₃SnH / AIBN / tetrahydrofuran / Heating

10: 100 percent / H₂ / 10percent Pd/C / ethanol

11: DIBAL / CH₂Cl₂ / -78 °C

12: tetrahydrofuran / Heating

13: 10percent HCl / tetrahydrofuran

14: SO₃*pyridine, Et₃N, DMSO / CH₂Cl₂

With pyridine; hydrogenchloride; manganese(IV) oxide; sodium chlorite; sodium tetrahydroborate; 2-methyl-but-2-ene; diethyl(2,2,6,6-tetramethylpiperidino)aluminium; pyridine-SO₃ complex; hydrogen; iodine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; potassium iodide; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(00)74124-4

Reference yield:

2-((3aR,5S,7aS)-2,2,7a-Trimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl)-propenal → (2S,5R)-2-Hydroxy-2-methyl-5-((R)-1-methyl-allyl)-cyclohexane-1,4-dione (139618-35-2)

Guidance literature:

Multi-step reaction with 8 steps

1: NaClO₂, NaHPO₄, 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol

2: I₂, KI, sat. NaHCO₃

3: 80 percent / n-Bu₃SnH / AIBN / tetrahydrofuran / Heating

4: 100 percent / H₂ / 10percent Pd/C / ethanol

5: DIBAL / CH₂Cl₂ / -78 °C

6: tetrahydrofuran / Heating

7: 10percent HCl / tetrahydrofuran

8: SO₃*pyridine, Et₃N, DMSO / CH₂Cl₂

With hydrogenchloride; sodium chlorite; 2-methyl-but-2-ene; pyridine-SO₃ complex; hydrogen; iodine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; potassium iodide; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; ethanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)74124-4

Reference yield:

(3aR,5S,7aS)-2,2,7a-Trimethyl-5-(2-methyl-oxiranyl)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxole (139618-31-8,139618-54-5) → (2S,5R)-2-Hydroxy-2-methyl-5-((R)-1-methyl-allyl)-cyclohexane-1,4-dione (139618-35-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 69 percent / diethylaluminum 2,2,6,6-tetramethylpiperidide / benzene / 0 °C

2: MnO₂ / CH₂Cl₂

3: NaClO₂, NaHPO₄, 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol

4: I₂, KI, sat. NaHCO₃

5: 80 percent / n-Bu₃SnH / AIBN / tetrahydrofuran / Heating

6: 100 percent / H₂ / 10percent Pd/C / ethanol

7: DIBAL / CH₂Cl₂ / -78 °C

8: tetrahydrofuran / Heating

9: 10percent HCl / tetrahydrofuran

10: SO₃*pyridine, Et₃N, DMSO / CH₂Cl₂

With hydrogenchloride; manganese(IV) oxide; sodium chlorite; 2-methyl-but-2-ene; diethyl(2,2,6,6-tetramethylpiperidino)aluminium; pyridine-SO₃ complex; hydrogen; iodine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; potassium iodide; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; ethanol; dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(00)74124-4

upstream raw materials:

(1R,2R,4S,6S)-(-)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol

(3aR,5S,7aS)-2,2,7a-Trimethyl-5-(2-methyl-oxiranyl)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxole

(3aS,4aR,7aR,8aR)-2,2,3a-Trimethyl-7-methylene-hexahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-6-one

2-((3aR,5S,7aS)-2,2,7a-Trimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl)-prop-2-en-1-ol

Downstream raw materials:

7S-Paeonimetabolin-I