(3aS,4S,7aR)-4-Bis(ethylthio)methyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>hexahydrobenzofuran-2(3H)-one

Base Information

• Chemical Name: (3aS,4S,7aR)-4-Bis(ethylthio)methyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>hexahydrobenzofuran-2(3H)-one
• CAS No.: 152492-25-6
• Molecular Formula: C₃₀H₄₂O₃S₂Si
• Molecular Weight: 542.879

Synonyms:(3aS,4S,7aR)-4-Bis(ethylthio)methyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>hexahydrobenzofuran-2(3H)-one

Chemical Property of (3aS,4S,7aR)-4-Bis(ethylthio)methyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>hexahydrobenzofuran-2(3H)-one

Chemical Property:

Purity/Quality:

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Technology Process of (3aS,4S,7aR)-4-Bis(ethylthio)methyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>hexahydrobenzofuran-2(3H)-one

There total 21 articles about (3aS,4S,7aR)-4-Bis(ethylthio)methyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>hexahydrobenzofuran-2(3H)-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:

(2R,3R,4R,5S)-4-(2-hydroxyethyl)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran (103537-73-1) → (3aS,4S,7aR)-4-Bis(ethylthio)methyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>hexahydrobenzofuran-2(3H)-one (152492-25-6)

Guidance literature:

Multi-step reaction with 21 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

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; 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:

(2'S,3aS,3'R,4'R,5'R,7aR)-2'-(Hydroxymethyl)-4',5'-(isopropylidenedioxy)spiro-2(3H)-one → (3aS,4S,7aR)-4-Bis(ethylthio)methyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>hexahydrobenzofuran-2(3H)-one (152492-25-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 89 percent / NaH / dimethylformamide / 2 h / Ambient temperature

2: 77 percent / 60percent aq. TFA / 72 h / 5 °C

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

4: NaBH₄ / methanol / 0.5 h / Ambient temperature

5: 83 percent / imidazole / dimethylformamide / 1.) r.t., 18 h, 2.) 50 deg C, 9 h

6: 85 percent / H₂ / Pd/C / ethanol / 26 h

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

8: conc. aq. HCl / 72 h / -15 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; sodium periodate; hydrogen; sodium hydride; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00075a021

Reference yield:

(2R,3R,4R,5S)-4-(2-Iodoethyl)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran (146383-47-3) → (3aS,4S,7aR)-4-Bis(ethylthio)methyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>hexahydrobenzofuran-2(3H)-one (152492-25-6)

Guidance literature:

Multi-step reaction with 20 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

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; 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

upstream raw materials:

(3aS,4S,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-oxo-octahydro-benzofuran-4-carbaldehyde

ethanethiol

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

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

Downstream raw materials:

(3aS,4R,7aR)-4-Methyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>hexahydrobenzofuran-2(3H)-one

(1R,2S,3S)-2-(2-Hydroxyethyl)-3-methyl-3-vinylcyclohexanol

(1R,2S,3S)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol

(1R,2S,3S)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-3-vinyl-cyclohexanol

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