(2S,3S)-3-Methyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanone

Base Information

Chemical Name:(2S,3S)-3-Methyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanone
CAS No.:152611-83-1
Molecular Formula:C₂₇H₃₆O₂Si
Molecular Weight:420.667
Hs Code.:

Synonyms:(2S,3S)-3-Methyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanone

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Chemical Property of (2S,3S)-3-Methyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanone

Chemical Property:

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Technology Process of (2S,3S)-3-Methyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanone

There total 28 articles about (2S,3S)-3-Methyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanone 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:

: 103537-73-1
(2R,3R,4R,5S)-4-(2-hydroxyethyl)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran

: 152611-83-1
(2S,3S)-3-Methyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanone

Guidance literature:: Multi-step reaction with 28 steps

1: 1.) Ph₃P, diethyl azodicarboxylate, 2.) MeI / 1.) THF, 0 deg C, 15 min, 2.) r.t., 8 h

2: NaH / tetrahydrofuran / 24 h / Heating

3: NaCl / dimethylsulfoxide; H₂O / 24 h / 160 °C

4: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

5: imidazole / dimethylformamide / 8 h / Ambient temperature

6: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 5 h, 2.) -78 deg C, 1 h

7: 1.) KN(TMS)2, 18-crown-6 / 1.) THF, toluene, -78 deg C, 20 min, 2.) THF, 5 deg C, 14 h

8: 100 percent / n-Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

9: 95 percent / PCC, molecular sieves / CH₂Cl₂ / 0.5 h / Ambient temperature

10: Sm(II) iodide, HMPA, 2-propanol / tetrahydrofuran / 1 h / Ambient temperature

11: 80 percent / 1M aq. HCl / tetrahydrofuran / 28 h / 5 °C

12: aq. NaIO₄ / methanol / 0.83 h / Ambient temperature

13: NaBH₄ / methanol / 0.67 h / 0 °C

14: 89 percent / NaH / dimethylformamide / 2 h / Ambient temperature

15: 77 percent / 60percent aq. TFA / 72 h / 5 °C

16: aq. NaIO₄ / methanol / 4 h / Ambient temperature

17: NaBH₄ / methanol / 0.5 h / Ambient temperature

18: 83 percent / imidazole / dimethylformamide / 1.) r.t., 18 h, 2.) 50 deg C, 9 h

19: 85 percent / H₂ / Pd/C / ethanol / 26 h

20: aq. NaIO₄ / methanol / 0.75 h / Ambient temperature

21: conc. aq. HCl / 72 h / -15 °C

22: 95 percent / Raney nickel T-4 / ethanol / 6.5 h / Heating

23: 85 percent / n-Bu₄NF / tetrahydrofuran / 10 h / Ambient temperature

24: PCC, molecular sieves / CH₂Cl₂ / 0.83 h / Ambient temperature

25: tetrahydrofuran / 0.17 h / Ambient temperature

26: 99 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / Ambient temperature

27: imidazole / dimethylformamide / 14.5 h

28: PCC, molecular sieves / CH₂Cl₂ / 1.25 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; molecular sieve; samarium diiodide; 18-crown-6 ether; Raney nickel T-4; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; sodium hydride; ozone; triphenylphosphine; isopropyl alcohol; pyridinium chlorochromate; trifluoroacetic acid; sodium chloride; diethylazodicarboxylate; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo00075a021

Reference yield:

: 146383-47-3
(2R,3R,4R,5S)-4-(2-Iodoethyl)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran

: 152611-83-1
(2S,3S)-3-Methyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanone

Guidance literature:: Multi-step reaction with 27 steps

1: NaH / tetrahydrofuran / 24 h / Heating

2: NaCl / dimethylsulfoxide; H₂O / 24 h / 160 °C

3: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

4: imidazole / dimethylformamide / 8 h / Ambient temperature

5: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 5 h, 2.) -78 deg C, 1 h

6: 1.) KN(TMS)2, 18-crown-6 / 1.) THF, toluene, -78 deg C, 20 min, 2.) THF, 5 deg C, 14 h

7: 100 percent / n-Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

8: 95 percent / PCC, molecular sieves / CH₂Cl₂ / 0.5 h / Ambient temperature

9: Sm(II) iodide, HMPA, 2-propanol / tetrahydrofuran / 1 h / Ambient temperature

10: 80 percent / 1M aq. HCl / tetrahydrofuran / 28 h / 5 °C

11: aq. NaIO₄ / methanol / 0.83 h / Ambient temperature

12: NaBH₄ / methanol / 0.67 h / 0 °C

13: 89 percent / NaH / dimethylformamide / 2 h / Ambient temperature

14: 77 percent / 60percent aq. TFA / 72 h / 5 °C

15: aq. NaIO₄ / methanol / 4 h / Ambient temperature

16: NaBH₄ / methanol / 0.5 h / Ambient temperature

17: 83 percent / imidazole / dimethylformamide / 1.) r.t., 18 h, 2.) 50 deg C, 9 h

18: 85 percent / H₂ / Pd/C / ethanol / 26 h

19: aq. NaIO₄ / methanol / 0.75 h / Ambient temperature

20: conc. aq. HCl / 72 h / -15 °C

21: 95 percent / Raney nickel T-4 / ethanol / 6.5 h / Heating

22: 85 percent / n-Bu₄NF / tetrahydrofuran / 10 h / Ambient temperature

23: PCC, molecular sieves / CH₂Cl₂ / 0.83 h / Ambient temperature

24: tetrahydrofuran / 0.17 h / Ambient temperature

25: 99 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / Ambient temperature

26: imidazole / dimethylformamide / 14.5 h

27: PCC, molecular sieves / CH₂Cl₂ / 1.25 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; molecular sieve; samarium diiodide; 18-crown-6 ether; Raney nickel T-4; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; sodium hydride; ozone; triphenylphosphine; isopropyl alcohol; pyridinium chlorochromate; trifluoroacetic acid; sodium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo00075a021

Reference yield:

: C₁₅H₂₀O₆

: 152611-83-1
(2S,3S)-3-Methyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanone

Guidance literature:: Multi-step reaction with 16 steps

1: NaBH₄ / methanol / 0.67 h / 0 °C

2: 89 percent / NaH / dimethylformamide / 2 h / Ambient temperature

3: 77 percent / 60percent aq. TFA / 72 h / 5 °C

4: aq. NaIO₄ / methanol / 4 h / Ambient temperature

5: NaBH₄ / methanol / 0.5 h / Ambient temperature

6: 83 percent / imidazole / dimethylformamide / 1.) r.t., 18 h, 2.) 50 deg C, 9 h

7: 85 percent / H₂ / Pd/C / ethanol / 26 h

8: aq. NaIO₄ / methanol / 0.75 h / Ambient temperature

9: conc. aq. HCl / 72 h / -15 °C

10: 95 percent / Raney nickel T-4 / ethanol / 6.5 h / Heating

11: 85 percent / n-Bu₄NF / tetrahydrofuran / 10 h / Ambient temperature

12: PCC, molecular sieves / CH₂Cl₂ / 0.83 h / Ambient temperature

13: tetrahydrofuran / 0.17 h / Ambient temperature

14: 99 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / Ambient temperature

15: imidazole / dimethylformamide / 14.5 h

16: PCC, molecular sieves / CH₂Cl₂ / 1.25 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; molecular sieve; Raney nickel T-4; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; pyridinium chlorochromate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00075a021