(R)-5-[(1R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-pentyl]-3-phenylselanyl-dihydro-furan-2-one

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Chemical Name:(R)-5-[(1R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-pentyl]-3-phenylselanyl-dihydro-furan-2-one
CAS No.:115479-72-6
Molecular Formula:C₃₃H₄₂O₃SeSi
Molecular Weight:593.74
Hs Code.:

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Chemical Property of (R)-5-[(1R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-pentyl]-3-phenylselanyl-dihydro-furan-2-one

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Technology Process of (R)-5-[(1R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-pentyl]-3-phenylselanyl-dihydro-furan-2-one

There total 30 articles about (R)-5-[(1R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-pentyl]-3-phenylselanyl-dihydro-furan-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:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 115479-72-6,115511-71-2
(R)-5-[(1R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-pentyl]-3-phenylselanyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 25 steps

1: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

2: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

3: 30percent H₂O₂ / 0 °C

4: 1.) n-butyl lithium / 1.) THF, hexane, -78 deg C, 20 min; 2.) THF, hexane, -78 deg C, 30 min.

5: 1.) n-butyl lithium, hexamethyldisilazane 3.) oxodiperoxomolybdenum-pyridine-HMPA complex / 1.) THF, 0 deg C, 10 min; 2.) THF, -78 deg C, 20 min; 3.) THF, -60 deg C, 45 min.

6: 62 percent / Raney-nickel / methanol / 18 h / Ambient temperature

7: NaBH₄ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

8: dimethoxypropane, conc. HCl / 1.5 h / Ambient temperature

9: 95 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

10: 92 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

11: sodium methoxide / methanol / 0.5 h / 0 °C

12: 1.) n-butyl lithium, hexamethyldisilazane / 1.) THF, 0 deg C, 15 min; 2.) THF, RT, 1 h, 3.) THF, RT, 15 h

13: EDAC, DMAP / CH₂Cl₂ / 0.33 h

14: m-CPBA / CH₂Cl₂ / 0.33 h / -23 °C

15: pyridine, CaCO₃ / toluene / 1 h / Heating

16: 1.) CuBr*Me₂S / 1.) ether, 0 deg C, 10 min; 2.) ether, -23 deg C, 10 min.

17: LiAlH₄ / diethyl ether / 1 h / 25 °C

18: 86 percent / imidazole / dimethylformamide / 0.33 h / Ambient temperature

19: Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

20: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

21: 98 percent / 80percent aq. AcOH / 15 h / Ambient temperature

22: pyridine / CH₂Cl₂ / 1 h / Ambient temperature

23: NaOMe / methanol; CH₂Cl₂ / 0.33 h / Ambient temperature

24: 1.) hexamethyldisilazane, n-butyl lithium / 1.) THF, 0 deg C, 20 min; 2.) THF RT, 1 h, 3.) THF, RT, 15 h

25: EDAC / DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; MoO₅*pyridine*HMPA; dimethoxypropane; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; nickel; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

: 5336-08-3
D-Ribono-1,4-lactone

: 115479-72-6,115511-71-2
(R)-5-[(1R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-pentyl]-3-phenylselanyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 28 steps

1: imidazole / dimethylformamide / 1 h / -20 - -15 °C

2: tetrahydrofuran / 0.25 h / Ambient temperature

3: Raney nickel / tetrahydrofuran / 4 h / Heating

4: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

5: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

6: 30percent H₂O₂ / 0 °C

7: 1.) n-butyl lithium / 1.) THF, hexane, -78 deg C, 20 min; 2.) THF, hexane, -78 deg C, 30 min.

8: 1.) n-butyl lithium, hexamethyldisilazane 3.) oxodiperoxomolybdenum-pyridine-HMPA complex / 1.) THF, 0 deg C, 10 min; 2.) THF, -78 deg C, 20 min; 3.) THF, -60 deg C, 45 min.

9: 62 percent / Raney-nickel / methanol / 18 h / Ambient temperature

10: NaBH₄ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

11: dimethoxypropane, conc. HCl / 1.5 h / Ambient temperature

12: 95 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

13: 92 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

14: sodium methoxide / methanol / 0.5 h / 0 °C

15: 1.) n-butyl lithium, hexamethyldisilazane / 1.) THF, 0 deg C, 15 min; 2.) THF, RT, 1 h, 3.) THF, RT, 15 h

16: EDAC, DMAP / CH₂Cl₂ / 0.33 h

17: m-CPBA / CH₂Cl₂ / 0.33 h / -23 °C

18: pyridine, CaCO₃ / toluene / 1 h / Heating

19: 1.) CuBr*Me₂S / 1.) ether, 0 deg C, 10 min; 2.) ether, -23 deg C, 10 min.

20: LiAlH₄ / diethyl ether / 1 h / 25 °C

21: 86 percent / imidazole / dimethylformamide / 0.33 h / Ambient temperature

22: Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

23: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

24: 98 percent / 80percent aq. AcOH / 15 h / Ambient temperature

25: pyridine / CH₂Cl₂ / 1 h / Ambient temperature

26: NaOMe / methanol; CH₂Cl₂ / 0.33 h / Ambient temperature

27: 1.) hexamethyldisilazane, n-butyl lithium / 1.) THF, 0 deg C, 20 min; 2.) THF RT, 1 h, 3.) THF, RT, 15 h

28: EDAC / DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; MoO₅*pyridine*HMPA; dimethoxypropane; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; nickel; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

: 99315-75-0
(-)-5-O-(diphenyl-t-butylsilyl)-2,3-O-(thiocarbonyl)-D-ribono-1,4-lactone

: 115479-72-6,115511-71-2
(R)-5-[(1R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-pentyl]-3-phenylselanyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 26 steps

1: Raney nickel / tetrahydrofuran / 4 h / Heating

2: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

3: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

4: 30percent H₂O₂ / 0 °C

5: 1.) n-butyl lithium / 1.) THF, hexane, -78 deg C, 20 min; 2.) THF, hexane, -78 deg C, 30 min.

6: 1.) n-butyl lithium, hexamethyldisilazane 3.) oxodiperoxomolybdenum-pyridine-HMPA complex / 1.) THF, 0 deg C, 10 min; 2.) THF, -78 deg C, 20 min; 3.) THF, -60 deg C, 45 min.

7: 62 percent / Raney-nickel / methanol / 18 h / Ambient temperature

8: NaBH₄ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

9: dimethoxypropane, conc. HCl / 1.5 h / Ambient temperature

10: 95 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

11: 92 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

12: sodium methoxide / methanol / 0.5 h / 0 °C

13: 1.) n-butyl lithium, hexamethyldisilazane / 1.) THF, 0 deg C, 15 min; 2.) THF, RT, 1 h, 3.) THF, RT, 15 h

14: EDAC, DMAP / CH₂Cl₂ / 0.33 h

15: m-CPBA / CH₂Cl₂ / 0.33 h / -23 °C

16: pyridine, CaCO₃ / toluene / 1 h / Heating

17: 1.) CuBr*Me₂S / 1.) ether, 0 deg C, 10 min; 2.) ether, -23 deg C, 10 min.

18: LiAlH₄ / diethyl ether / 1 h / 25 °C

19: 86 percent / imidazole / dimethylformamide / 0.33 h / Ambient temperature

20: Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

21: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

22: 98 percent / 80percent aq. AcOH / 15 h / Ambient temperature

23: pyridine / CH₂Cl₂ / 1 h / Ambient temperature

24: NaOMe / methanol; CH₂Cl₂ / 0.33 h / Ambient temperature

25: 1.) hexamethyldisilazane, n-butyl lithium / 1.) THF, 0 deg C, 20 min; 2.) THF RT, 1 h, 3.) THF, RT, 15 h

26: EDAC / DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; MoO₅*pyridine*HMPA; dimethoxypropane; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; nickel; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)87683-3