4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-3,3-dimethyl-4-oxo-hept-6-enyl]-tetrahydro-pyran-2-one

Base Information

• Chemical Name: 4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-3,3-dimethyl-4-oxo-hept-6-enyl]-tetrahydro-pyran-2-one
• CAS No.: 935248-53-6
• Molecular Formula: C₃₈H₄₈O₆Si
• Molecular Weight: 628.881

Synonyms:4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-3,3-dimethyl-4-oxo-hept-6-enyl]-tetrahydro-pyran-2-one

Chemical Property of 4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-3,3-dimethyl-4-oxo-hept-6-enyl]-tetrahydro-pyran-2-one

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Technology Process of 4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-3,3-dimethyl-4-oxo-hept-6-enyl]-tetrahydro-pyran-2-one

There total 11 articles about 4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-3,3-dimethyl-4-oxo-hept-6-enyl]-tetrahydro-pyran-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: 86.0%

C38H50O6Si (935248-52-5) → 4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-3,3-dimethyl-4-oxo-hept-6-enyl]-tetrahydro-pyran-2-one (935248-53-6)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ja067305j

Reference yield:

9-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-7-(4-methoxy-benzyloxy)-8,8-dimethyl-nonanoic acid methyl ester (935248-47-8) → 4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-3,3-dimethyl-4-oxo-hept-6-enyl]-tetrahydro-pyran-2-one (935248-53-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / Otera's catalyst / hexane / 3 h / Heating

2: imidazole / dimethylformamide / 3 h / 50 °C

3: 3.4 g / AcOH / H₂O / 11 h / 20 °C

4: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

5: 1.42 g / In / dimethylformamide / 16 h / 20 °C

6: 86 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; indium; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; Otera's catalyst; In hexane; dichloromethane; water; N,N-dimethyl-formamide; 4: Dess-Martin oxidation / 6: Dess-Martin oxidation;

DOI:10.1021/ja067305j

Reference yield:

5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4-dimethyl-pentan-1-ol (935248-44-5) → 4-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-3,3-dimethyl-4-oxo-hept-6-enyl]-tetrahydro-pyran-2-one (935248-53-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: aq. NaOCl; NaHCO₃ / KBr; TEMPO / CH₂Cl₂ / 0.5 h

2.1: Ti(Oi-Pr)4; TiCl₄ / toluene / 0.33 h / -78 °C

2.2: 9.77 g / toluene / 0.5 h / -78 °C

3.1: 91 percent / (CH₃)4NBH(OAc)3; AcOH / acetonitrile / 40 h / -35 °C

4.1: 86 percent / Otera's catalyst / hexane / 3 h / Heating

5.1: imidazole / dimethylformamide / 3 h / 50 °C

6.1: 3.4 g / AcOH / H₂O / 11 h / 20 °C

7.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

8.1: 1.42 g / In / dimethylformamide / 16 h / 20 °C

9.1: 86 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; indium; sodium hypochlorite; titanium tetrachloride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; 2,2,6,6-tetramethyl-piperidine-N-oxyl; Otera's catalyst; potassium bromide; In hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 7.1: Dess-Martin oxidation / 9.1: Dess-Martin oxidation;

DOI:10.1021/ja067305j

upstream raw materials:

C₃₈H₅₀O₆Si

6-[4-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-butyl]-4-hydroxy-tetrahydropyran-2-one

6-[4-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-butyl]-4-[(1,1-dimethyl-ethyl)-diphenyl-silanyloxy]-tetrahydropyran-2-one

4-(tert-butyl-diphenyl-silanyloxy)-6-[4-hydroxy-2-(4-methoxy-benzyloxy)-3,3-dimethyl-butyl]-tetrahydropyran-2-one

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