4(R)-(tert-butyldiphenylsiloxy)-6(S)-<<2,4-dimethyl-6-phenoxy>methyl>tetrahydropyran-2-one

Base Information

• Chemical Name: 4(R)-(tert-butyldiphenylsiloxy)-6(S)-<<2,4-dimethyl-6-phenoxy>methyl>tetrahydropyran-2-one
• CAS No.: 136007-88-0
• Molecular Formula: C₄₃H₅₉NO₅Si
• Molecular Weight: 698.031

Synonyms:4(R)-(tert-butyldiphenylsiloxy)-6(S)-<<2,4-dimethyl-6-phenoxy>methyl>tetrahydropyran-2-one

Chemical Property of 4(R)-(tert-butyldiphenylsiloxy)-6(S)-<<2,4-dimethyl-6-phenoxy>methyl>tetrahydropyran-2-one

Chemical Property:

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Technology Process of 4(R)-(tert-butyldiphenylsiloxy)-6(S)-<<2,4-dimethyl-6-phenoxy>methyl>tetrahydropyran-2-one

There total 10 articles about 4(R)-(tert-butyldiphenylsiloxy)-6(S)-<<2,4-dimethyl-6-phenoxy>methyl>tetrahydropyran-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:

[(2S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-methanol (110772-23-1) → 4(R)-(tert-butyldiphenylsiloxy)-6(S)-<<2,4-dimethyl-6-phenoxy>methyl>tetrahydropyran-2-one (136007-88-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

2: 90 percent / NaI / acetone / 24 h / Heating

3: 74 percent / K₂CO₃ / dimethylsulfoxide / 60 °C

4: 76 percent / glacial acetic acid / tetrahydrofuran / Heating

5: tetra-n-butylammonium iodide, N-iodosuccinimide / CH₂Cl₂ / 20 h / Ambient temperature

6: 546 mg / 48percent aq. HF / 50 h / 25 °C

With pyridine; N-iodo-succinimide; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; sodium iodide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetone;

DOI:10.1021/jm00114a004

Reference yield:

2,4-dimethyl-6-(cyclohexylcarbonyl)phenol (115807-77-7) → 4(R)-(tert-butyldiphenylsiloxy)-6(S)-<<2,4-dimethyl-6-phenoxy>methyl>tetrahydropyran-2-one (136007-88-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / NaBH₄ / H₂O / 0.5 h / 20 °C

2: 74 percent / K₂CO₃ / dimethylsulfoxide / 60 °C

3: 76 percent / glacial acetic acid / tetrahydrofuran / Heating

4: tetra-n-butylammonium iodide, N-iodosuccinimide / CH₂Cl₂ / 20 h / Ambient temperature

5: 546 mg / 48percent aq. HF / 50 h / 25 °C

With sodium tetrahydroborate; N-iodo-succinimide; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1021/jm00114a004

Reference yield:

1-<(cyclohexylcarbonyl)oxy>-2,4-dimethylbenzene (136007-80-2) → 4(R)-(tert-butyldiphenylsiloxy)-6(S)-<<2,4-dimethyl-6-phenoxy>methyl>tetrahydropyran-2-one (136007-88-0)

Guidance literature:

Multi-step reaction with 6 steps

1: AlCl₃ / 1 h / 150 °C

2: 88 percent / NaBH₄ / H₂O / 0.5 h / 20 °C

3: 74 percent / K₂CO₃ / dimethylsulfoxide / 60 °C

4: 76 percent / glacial acetic acid / tetrahydrofuran / Heating

5: tetra-n-butylammonium iodide, N-iodosuccinimide / CH₂Cl₂ / 20 h / Ambient temperature

6: 546 mg / 48percent aq. HF / 50 h / 25 °C

With sodium tetrahydroborate; N-iodo-succinimide; aluminium trichloride; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1021/jm00114a004

upstream raw materials:

2,2-dimethylbutyronitrile

4(R)-(tert-butyldiphenylsiloxy)-6(S)-<<2,4-dimethyl-6-(cyclohexylhydroxymethyl)phenoxy>methyl>tetrahydropyran-2-one

[(2S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-methanol

1-<(cyclohexylcarbonyl)oxy>-2,4-dimethylbenzene

Downstream raw materials:

Sodium; (3R,5S)-6-{2-[(S)-cyclohexyl-(2,2-dimethyl-butyrylamino)-methyl]-4,6-dimethyl-phenoxy}-3,5-dihydroxy-hexanoate

N-{(S)-Cyclohexyl-[2-((2S,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-ylmethoxy)-3,5-dimethyl-phenyl]-methyl}-2,2-dimethyl-butyramide

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