4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-2-one

Base Information

Chemical Name:4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-2-one
CAS No.:916912-79-3
Molecular Formula:C₁₃H₂₈O₂Si
Molecular Weight:244.45
Hs Code.:

4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-5-methyl-hexan-2-one

Synonyms:4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-2-one

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Chemical Property of 4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-2-one

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Technology Process of 4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-2-one

There total 1 articles about 4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-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:

: 38836-21-4,65651-63-0
(S)-4-hydroxy-5-methylhexan-2-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 916912-79-3
4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-2-one

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 24h;
DOI:10.1002/chem.200600599

Reference yield:

: 916912-79-3
4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-2-one

: (E)-(2S,3S,5R,7S,10S,16S,19S,22S,27S)-16-((S)-sec-Butyl)-3-hydroxy-7-isopropyl-22-(4-methoxy-benzyl)-2,5,17,19,20,25-hexamethyl-8,29-dioxa-14,17,20,23,30-pentaaza-tricyclo[25.2.1.0^10,14]triaconta-1⁽³⁰⁾,25-diene-9,15,18,21,24-pentaone

Guidance literature:: Multi-step reaction with 19 steps

1.1: LDA / hexane; tetrahydrofuran / 0.33 h / -78 °C

1.2: hexane; tetrahydrofuran / 1 h / -78 °C

2.1: 8.35 g / aq. HF / acetonitrile / 20 °C

3.1: H₂ / Pd/C / dioxane / 12 h / 20 °C / 760 Torr

3.2: 83 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

4.1: pyridine / CH₂Cl₂ / 0 °C

5.1: aq. K₂CO₃ / methanol / 5 h

6.1: Dess-Martin reagent / CH₂Cl₂ / 3 h / 0 °C

7.1: CF₃SO₃H; Et₃B; DIPEA / hexane; CH₂Cl₂ / 0.5 h / -10 °C

7.2: 91 percent / TiCl₄ / hexane; CH₂Cl₂ / 2 h

8.1: LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

9.1: PPTs / 24 h

10.1: 82 percent / 2,4,6-trichlorobenzoyl chloride; DIPEA; DMAP / benzene

11.1: TsOH / methanol

12.1: 2,2,6,6-tetramethylpiperidinyloxyl; KBr; NaHCO₃ / NaClO / CH₂Cl₂; H₂O / 1 h

13.1: NaClO₂; NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 1 h

14.1: HATU; DIPEA / CH₂Cl₂ / 24 h

15.1: 86 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 3 h / -78 °C

16.1: N-methylaniline / [Pd(PPh₃)4] / tetrahydrofuran / 2 h

17.1: HATU; DIPEA / CH₂Cl₂ / 48 h / 20 °C

18.1: tetrabutylammonium fluoride / tetrahydrofuran

19.1: HATU; DIPEA / CH₂Cl₂

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl; triethyl borane; trifluorormethanesulfonic acid; diethylamino-sulfur trifluoride; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; N-methylaniline; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium bromide; lithium diisopropyl amide; sodium hypochlorite; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; benzene; 1.2: Peterson reaction / 6.1: Dess-Martin oxidation;
DOI:10.1002/chem.200600599

Reference yield:

: 916912-79-3
4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexan-2-one

: pyrrolidine-2-carboxylic acid 6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-oxazol-2-yl)-5-hydroxy-1-isopropyl-3-methyl-heptyl ester

Guidance literature:: Multi-step reaction with 18 steps

1.1: LDA / hexane; tetrahydrofuran / 0.33 h / -78 °C

1.2: hexane; tetrahydrofuran / 1 h / -78 °C

2.1: 8.35 g / aq. HF / acetonitrile / 20 °C

3.1: H₂ / Pd/C / dioxane / 12 h / 20 °C / 760 Torr

3.2: 83 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

4.1: pyridine / CH₂Cl₂ / 0 °C

5.1: aq. K₂CO₃ / methanol / 5 h

6.1: Dess-Martin reagent / CH₂Cl₂ / 3 h / 0 °C

7.1: CF₃SO₃H; Et₃B; DIPEA / hexane; CH₂Cl₂ / 0.5 h / -10 °C

7.2: 91 percent / TiCl₄ / hexane; CH₂Cl₂ / 2 h

8.1: LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

9.1: PPTs / 24 h

10.1: 82 percent / 2,4,6-trichlorobenzoyl chloride; DIPEA; DMAP / benzene

11.1: TsOH / methanol

12.1: 2,2,6,6-tetramethylpiperidinyloxyl; KBr; NaHCO₃ / NaClO / CH₂Cl₂; H₂O / 1 h

13.1: NaClO₂; NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 1 h

14.1: HATU; DIPEA / CH₂Cl₂ / 24 h

15.1: 86 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 3 h / -78 °C

16.1: N-methylaniline / [Pd(PPh₃)4] / tetrahydrofuran / 2 h

17.1: HATU; DIPEA / CH₂Cl₂ / 48 h / 20 °C

18.1: tetrabutylammonium fluoride / tetrahydrofuran

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl; triethyl borane; trifluorormethanesulfonic acid; diethylamino-sulfur trifluoride; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; N-methylaniline; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium bromide; lithium diisopropyl amide; sodium hypochlorite; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; benzene; 1.2: Peterson reaction / 6.1: Dess-Martin oxidation;
DOI:10.1002/chem.200600599