(S)-3-Methyl-3-((1S,2S)-1,2,6-trimethyl-6-triethylsilanyloxy-heptyl)-cyclohexanone

Base Information

Chemical Name:(S)-3-Methyl-3-((1S,2S)-1,2,6-trimethyl-6-triethylsilanyloxy-heptyl)-cyclohexanone
CAS No.:248916-65-6
Molecular Formula:C₂₃H₄₆O₂Si
Molecular Weight:382.703
Hs Code.:

Synonyms:(S)-3-Methyl-3-((1S,2S)-1,2,6-trimethyl-6-triethylsilanyloxy-heptyl)-cyclohexanone

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Chemical Property of (S)-3-Methyl-3-((1S,2S)-1,2,6-trimethyl-6-triethylsilanyloxy-heptyl)-cyclohexanone

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Technology Process of (S)-3-Methyl-3-((1S,2S)-1,2,6-trimethyl-6-triethylsilanyloxy-heptyl)-cyclohexanone

There total 15 articles about (S)-3-Methyl-3-((1S,2S)-1,2,6-trimethyl-6-triethylsilanyloxy-heptyl)-cyclohexanone 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: 70.0%

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 248916-64-5
(S)-3-((1S,2S)-6-Hydroxy-1,2,6-trimethyl-heptyl)-3-methyl-cyclohexanone

: 248916-65-6
(S)-3-Methyl-3-((1S,2S)-1,2,6-trimethyl-6-triethylsilanyloxy-heptyl)-cyclohexanone

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/jm980736v

Reference yield:

: (2R/S,3R)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butanoic acid

: 248916-65-6
(S)-3-Methyl-3-((1S,2S)-1,2,6-trimethyl-6-triethylsilanyloxy-heptyl)-cyclohexanone

Guidance literature:: Multi-step reaction with 14 steps

1.1: LiAlH₄ / tetrahydrofuran / 43 h / Heating

2.1: 97 percent / SO₃*Py; Et₃N; DMSO / CH₂Cl₂ / 1.5 h / -10 - -4 °C

3.1: DBU / CH₂Cl₂ / 62 h / 20 °C

4.1: NaBH₄ / methanol / 0.25 h / -10 °C

5.1: 78 percent / pyridine / 24 h / 0 °C

6.1: 80 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

7.1: 9-BBN / tetrahydrofuran / 48 h / Heating

7.2: 95 percent / 30 percent H₂O₂; 6 N aq. NaOH / ethanol / 1.5 h / 55 °C

8.1: 76 percent / imidazole; DMAP / dimethylformamide / 16 h / 20 °C

9.1: 85 percent / cyclohexene / 20 percent Pd(OH)2/C / ethanol / 6 h / Heating

10.1: 93 percent / pyridine / 19 h / 20 °C

11.1: NaH; DMSO / 0.75 h / 20 °C

11.2: 48 percent / dimethylsulfoxide / 0.75 h

12.1: 90 percent / H₂ / 5 percent Rh/Al₂O₃ / ethyl acetate / 4 h / 20 °C / 750.06 Torr

13.1: 40 percent / PDC / CH₂Cl₂ / 24 h / 20 °C

14.1: 70 percent / Et₃N / CH₂Cl₂ / 4 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO₃ complex; hydrogen; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; cyclohexene; palladium dihydroxide; Rh/Al₂O₃; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Oxidation / 3.1: Isomerization / 4.1: Reduction / 5.1: Tosylation / 6.1: reductive cleavae / 7.1: hydroboration / 7.2: Oxidation / 8.1: silylation / 9.1: debenzylation / 10.1: Tosylation / 11.1: Metallation / 11.2: Substitution / 12.1: Catalytic hydrogenation / 13.1: Oxidation / 14.1: silylation;
DOI:10.1021/jm980736v

Reference yield:

: 248916-36-1
(2R,3R)-4-Benzyloxy-3-methyl-2-((S)-1-methyl-cyclohex-2-enyl)-butyraldehyde

: 248916-65-6
(S)-3-Methyl-3-((1S,2S)-1,2,6-trimethyl-6-triethylsilanyloxy-heptyl)-cyclohexanone

Guidance literature:: Multi-step reaction with 12 steps

1.1: DBU / CH₂Cl₂ / 62 h / 20 °C

2.1: NaBH₄ / methanol / 0.25 h / -10 °C

3.1: 78 percent / pyridine / 24 h / 0 °C

4.1: 80 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

5.1: 9-BBN / tetrahydrofuran / 48 h / Heating

5.2: 95 percent / 30 percent H₂O₂; 6 N aq. NaOH / ethanol / 1.5 h / 55 °C

6.1: 76 percent / imidazole; DMAP / dimethylformamide / 16 h / 20 °C

7.1: 85 percent / cyclohexene / 20 percent Pd(OH)2/C / ethanol / 6 h / Heating

8.1: 93 percent / pyridine / 19 h / 20 °C

9.1: NaH; DMSO / 0.75 h / 20 °C

9.2: 48 percent / dimethylsulfoxide / 0.75 h

10.1: 90 percent / H₂ / 5 percent Rh/Al₂O₃ / ethyl acetate / 4 h / 20 °C / 750.06 Torr

11.1: 40 percent / PDC / CH₂Cl₂ / 24 h / 20 °C

12.1: 70 percent / Et₃N / CH₂Cl₂ / 4 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; cyclohexene; palladium dihydroxide; Rh/Al₂O₃; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Isomerization / 2.1: Reduction / 3.1: Tosylation / 4.1: reductive cleavae / 5.1: hydroboration / 5.2: Oxidation / 6.1: silylation / 7.1: debenzylation / 8.1: Tosylation / 9.1: Metallation / 9.2: Substitution / 10.1: Catalytic hydrogenation / 11.1: Oxidation / 12.1: silylation;
DOI:10.1021/jm980736v