(5S,6S)-6-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-3,3,5-trimethyltetrahydro-2H-pyran-2-one

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Chemical Name:(5S,6S)-6-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-3,3,5-trimethyltetrahydro-2H-pyran-2-one
CAS No.:468738-78-5
Molecular Formula:C₂₇H₃₈O₃Si
Molecular Weight:438.682
Hs Code.:

Synonyms:

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Chemical Property of (5S,6S)-6-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-3,3,5-trimethyltetrahydro-2H-pyran-2-one

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Technology Process of (5S,6S)-6-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-3,3,5-trimethyltetrahydro-2H-pyran-2-one

There total 8 articles about (5S,6S)-6-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-3,3,5-trimethyltetrahydro-2H-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:

: 92817-88-4
(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

: 468738-78-5
(5S,6S)-6-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-3,3,5-trimethyltetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: molecular sieves 4 Angstroem / toluene / -78 °C

1.2: 0.22 g / NaBH₄; NaOH / toluene; ethanol; H₂O / 2 h / 0 °C

2.1: 80 percent / diisopropylethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / -78 °C

3.1: 96 percent / titanium(IV) isopropoxide / bis(tricyclohexylphophine)benzylidiene Ru(IV) dichloride / CH₂Cl₂ / Heating

4.1: 92 percent / hydrogen / Pd(OH)2 / ethyl acetate / 20 °C

5.1: LDA / hexane; tetrahydrofuran / 2 h / -78 °C

5.2: 0.044 g / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 0.33 h / -78 °C

With titanium(IV) isopropylate; dmap; 4 A molecular sieve; hydrogen; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium dihydroxide; Grubbs catalyst first generation; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; toluene;
DOI:10.1016/S0040-4020(02)00555-0

Reference yield:

: 95514-04-8
(R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol

: 468738-78-5
(5S,6S)-6-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-3,3,5-trimethyltetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 100 percent / DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / 1.25 h / -78 - 0 °C

2.1: molecular sieves 4 Angstroem / toluene / -78 °C

2.2: 0.22 g / NaBH₄; NaOH / toluene; ethanol; H₂O / 2 h / 0 °C

3.1: 80 percent / diisopropylethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / -78 °C

4.1: 96 percent / titanium(IV) isopropoxide / bis(tricyclohexylphophine)benzylidiene Ru(IV) dichloride / CH₂Cl₂ / Heating

5.1: 92 percent / hydrogen / Pd(OH)2 / ethyl acetate / 20 °C

6.1: LDA / hexane; tetrahydrofuran / 2 h / -78 °C

6.2: 0.044 g / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 0.33 h / -78 °C

With titanium(IV) isopropylate; dmap; oxalyl dichloride; 4 A molecular sieve; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium dihydroxide; Grubbs catalyst first generation; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; toluene; 1.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00555-0

Reference yield:

: 106357-24-8
(3S,4S,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene

: 468738-78-5
(5S,6S)-6-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-3,3,5-trimethyltetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 80 percent / diisopropylethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / -78 °C

2.1: 96 percent / titanium(IV) isopropoxide / bis(tricyclohexylphophine)benzylidiene Ru(IV) dichloride / CH₂Cl₂ / Heating

3.1: 92 percent / hydrogen / Pd(OH)2 / ethyl acetate / 20 °C

4.1: LDA / hexane; tetrahydrofuran / 2 h / -78 °C

4.2: 0.044 g / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 0.33 h / -78 °C

With titanium(IV) isopropylate; dmap; hydrogen; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium dihydroxide; Grubbs catalyst first generation; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(02)00555-0