(4S,6S)-6-methyl-4-(phenylmethoxy)dodecan-2-one

Base Information

• Chemical Name: (4S,6S)-6-methyl-4-(phenylmethoxy)dodecan-2-one
• CAS No.: 309929-59-7
• Molecular Formula: C₂₀H₃₂O₂
• Molecular Weight: 304.473
• Mol file: 309929-59-7.mol

Synonyms:(4S,6S)-6-methyl-4-(phenylmethoxy)dodecan-2-one

Chemical Property of (4S,6S)-6-methyl-4-(phenylmethoxy)dodecan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6S)-6-methyl-4-(phenylmethoxy)dodecan-2-one

There total 18 articles about (4S,6S)-6-methyl-4-(phenylmethoxy)dodecan-2-one 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:

(4S,6S)-4-Benzyloxy-6-methyl-dodecan-2-ol → (4S,6S)-6-methyl-4-(phenylmethoxy)dodecan-2-one (309929-59-7)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 20 ℃;

DOI:10.1021/jo0055436

Reference yield:

((2S,3S)-3-(2-(benzyloxy)ethyl)oxiran-2-yl)methanol (111466-55-8) → (4S,6S)-6-methyl-4-(phenylmethoxy)dodecan-2-one (309929-59-7)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 88 percent / Red-Al / tetrahydrofuran; toluene / 0 °C

2.1: POCl₃ / CH₂Cl₂ / 4 h / 0 °C

3.1: NaH; Bu₄NI / tetrahydrofuran / 24 h / 20 °C

4.1: 0.26 g / aq. HCl / methanol / 0.08 h / 20 °C

5.1: SO₃-pyridine; Et₃N / dimethylformamide; CH₂Cl₂ / 20 °C

6.1: tetrahydrofuran / -78 °C

7.1: 0.19 g / PCC; NaOAc / CH₂Cl₂ / 20 °C

8.1: hexane; tetrahydrofuran / -78 °C

9.1: Co₂(CO)8 / CH₂Cl₂ / 20 °C

9.2: BF₃*OEt₂ / CH₂Cl₂ / -20 °C

9.3: 0.13 g / CAN / acetone / 0 °C

10.1: 100 percent / H₂ / Pd/C / ethyl acetate / 2 h / 20 °C / 760.05 Torr

11.1: Et₃N / CH₂Cl₂ / 0 - 20 °C

12.1: 18-crown-6 / benzene / 12 h / Heating

13.1: 99 mg / NaH / methanol; CH₂Cl₂ / 1 h / 20 °C

14.1: CSA / CH₂Cl₂ / 20 °C

15.1: 94 mg / DIBAL-H / CH₂Cl₂; cyclohexane / 0 °C

16.1: SO₃-pyridine; Et₃N / dimethylformamide; CH₂Cl₂ / 0 °C

17.1: tetrahydrofuran / -78 °C

18.1: 71 mg / PCC; NaOAc / CH₂Cl₂ / 20 °C

With hydrogenchloride; dicobalt octacarbonyl; 18-crown-6 ether; pyridine-SO₃ complex; camphor-10-sulfonic acid; hydrogen; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 1.1: Ring cleavage / 2.1: Etherification / 3.1: Alkylation / 4.1: Hydrogenolysis / 5.1: Oxidation / 6.1: Grignard reaction / 7.1: Oxidation / 8.1: Substitution / 9.1: Metallation / 9.2: Reduction / 9.3: demetallation / 10.1: Catalytic hydrogenation / 11.1: Substitution / 12.1: Substitution / 13.1: Deacetylation / 14.1: Substitution / 15.1: Ring cleavage / 16.1: Oxidation / 17.1: Grignard reaction / 18.1: Oxidation;

DOI:10.1021/jo0055436

Reference yield:

(3R)-5-(phenylmethoxy)pentane-1,3-diol (128524-85-6) → (4S,6S)-6-methyl-4-(phenylmethoxy)dodecan-2-one (309929-59-7)

Guidance literature:

Multi-step reaction with 17 steps

1.1: POCl₃ / CH₂Cl₂ / 4 h / 0 °C

2.1: NaH; Bu₄NI / tetrahydrofuran / 24 h / 20 °C

3.1: 0.26 g / aq. HCl / methanol / 0.08 h / 20 °C

4.1: SO₃-pyridine; Et₃N / dimethylformamide; CH₂Cl₂ / 20 °C

5.1: tetrahydrofuran / -78 °C

6.1: 0.19 g / PCC; NaOAc / CH₂Cl₂ / 20 °C

7.1: hexane; tetrahydrofuran / -78 °C

8.1: Co₂(CO)8 / CH₂Cl₂ / 20 °C

8.2: BF₃*OEt₂ / CH₂Cl₂ / -20 °C

8.3: 0.13 g / CAN / acetone / 0 °C

9.1: 100 percent / H₂ / Pd/C / ethyl acetate / 2 h / 20 °C / 760.05 Torr

10.1: Et₃N / CH₂Cl₂ / 0 - 20 °C

11.1: 18-crown-6 / benzene / 12 h / Heating

12.1: 99 mg / NaH / methanol; CH₂Cl₂ / 1 h / 20 °C

13.1: CSA / CH₂Cl₂ / 20 °C

14.1: 94 mg / DIBAL-H / CH₂Cl₂; cyclohexane / 0 °C

15.1: SO₃-pyridine; Et₃N / dimethylformamide; CH₂Cl₂ / 0 °C

16.1: tetrahydrofuran / -78 °C

17.1: 71 mg / PCC; NaOAc / CH₂Cl₂ / 20 °C

With hydrogenchloride; dicobalt octacarbonyl; 18-crown-6 ether; pyridine-SO₃ complex; camphor-10-sulfonic acid; hydrogen; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; pyridinium chlorochromate; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; ethyl acetate; N,N-dimethyl-formamide; benzene; 1.1: Etherification / 2.1: Alkylation / 3.1: Hydrogenolysis / 4.1: Oxidation / 5.1: Grignard reaction / 6.1: Oxidation / 7.1: Substitution / 8.1: Metallation / 8.2: Reduction / 8.3: demetallation / 9.1: Catalytic hydrogenation / 10.1: Substitution / 11.1: Substitution / 12.1: Deacetylation / 13.1: Substitution / 14.1: Ring cleavage / 15.1: Oxidation / 16.1: Grignard reaction / 17.1: Oxidation;

DOI:10.1021/jo0055436

upstream raw materials:

((2S,3S)-3-(2-(benzyloxy)ethyl)oxiran-2-yl)methanol

(3R)-5-(phenylmethoxy)pentane-1,3-diol

(3S,6S)-5-methylundecane-1,3-diol

(5S,3R)-5-methylundecane-1,3-diol