C₃₅H₅₀O₉Si

Base Information

Chemical Name:C₃₅H₅₀O₉Si
CAS No.:168421-82-7
Molecular Formula:C₃₅H₅₀O₉Si
Molecular Weight:642.862
Hs Code.:

C<sub>35</sub>H<sub>50</sub>O<sub>9</sub>Si

Synonyms:C₃₅H₅₀O₉Si

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Chemical Property of C₃₅H₅₀O₉Si

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Technology Process of C₃₅H₅₀O₉Si

There total 40 articles about C₃₅H₅₀O₉Si 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:

: 878-47-7,4242-00-6,34996-06-0,50302-16-4,70191-02-5,34996-05-9
(4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one

: 168421-82-7
C₃₅H₅₀O₉Si

Guidance literature:: Multi-step reaction with 38 steps

1: 1.) Ac₂O, DMAP, Py, 2.) naphthalenesulfonic acid, 3.) NaOMe

2: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

3: 1.) BH₃*THF, 2.) aq. H₂O₂, aq. NaOH, 3.) pyridinium dichromate

4: 1.) KHMDS / 1.) THF, -78 deg C, 2.) THF

5: 73 percent / Pd(OH)2, Ph₃P, Hunig's base / dimethylformamide

6: 99 percent / DIBAL / hexane / -78 °C

7: 45 percent / N-methylmorpholine N-oxide monohydrate (NMO), OsO₄, H₂O / acetone; propan-2-ol / 15 h / Ambient temperature

8: Py / CH₂Cl₂ / 3 h / Ambient temperature

9: CH₂Cl₂ / 1.5 h / Ambient temperature

10: ethane-1,2-diol; CH₂Cl₂ / 14.5 h / Heating

11: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, 0 deg C 0.5 h, 2.) THF, RT, 4 h

12: 84 percent / TsOH / acetone; H₂O / 2.5 h / Heating

13: 84 percent / Et₃N / CH₂Cl₂; H₂O / 4 h / -78 °C / Heating

14: 1.) 3,3-dimethyldioxirane, 2.) camphorosulfonic acid / 1.) CH₂Cl₂, Me₂CO, 10 min, 2.) Me₂CO, 0.5 h

15: 97 percent / Pb(OAc)4 / benzene / 0.17 h / 0 °C

16: 97 percent / collidinium p-toluene sulfonate (CPTS) / 10 h / Heating

17: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

18: 88 percent / Bu₃P / tetrahydrofuran / 0.25 h / Ambient temperature

19: 90 percent / aq. H₂O₂ / tetrahydrofuran / 12 h / Ambient temperature

20: 1.) O₃, NaHCO₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 0.5 h

21: 1.) tBuLi, 3.) tetrabutylammonium fluoride

22: 80 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 11 h / Ambient temperature

23: 65 percent / H₂ / Pd/C / ethanol / 1.25 h / -5 °C

24: 81 percent / NaH / dimethylformamide

25: 93 percent / L-selectride / tetrahydrofuran / 1.25 h / -78 °C

26: 98 percent / KHMDS / tetrahydrofuran / 0.17 h / -78 °C

27: 96 percent / aq. pyridinium p-toluenesulfonate / acetone / 9 h / 75 °C

28: 77 percent / tetrahydrofuran / 0.42 h / -78 - 0 °C

29: 46 percent / Pd(Ph₃P)4, K₂CO₃, molecular sieves 4A / acetonitrile / 16.5 h / 90 °C

30: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

31: 92 percent / Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

32: 45 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 10.25 h / Ambient temperature

33: 82 percent / H₂, Pd(OAc)2 / ethanol / 10 h

34: 66 percent / Py, DMAP / 16 h / Ambient temperature

35: 93 percent / tetrahydrofuran; diethyl ether / 0.03 h / -78 °C

36: 1.) OsO₄, Py, 2.) Pb(OAc)4 / 1.) 105 deg C, 2.) C₆H₆, MeOH, 0 deg C, 5 min

37: 92 percent / SmI₂, Ac₂O / tetrahydrofuran / 0.17 h / -78 °C

38: 1.) KOtBu, 2.) (PhSeO)2O, 3.) KOtBu

With pyridine; 2,6-dimethylpyridine; lead(IV) acetate; dmap; palladium diacetate; palladium dihydroxide; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; samarium diiodide; borane-THF; tributylphosphine; collidinium p-toluene sulfonate; (PhSeO)2O; 4 A molecular sieve; naphthalenesulfonic acid; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; tert.-butyl lithium; sodium methylate; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; acetic anhydride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; L-Selectride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; isopropyl alcohol; acetone; acetonitrile; benzene;
DOI:10.1021/ja952692a

Reference yield:

: 155681-64-4
(4'aS,5'S,8'aS)-5'-(tert-Butyl-dimethyl-silanyloxy)-4'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-one

: 168421-82-7
C₃₅H₅₀O₉Si

Guidance literature:: Multi-step reaction with 35 steps

1: 1.) KHMDS / 1.) THF, -78 deg C, 2.) THF

2: 73 percent / Pd(OH)2, Ph₃P, Hunig's base / dimethylformamide

3: 99 percent / DIBAL / hexane / -78 °C

4: 45 percent / N-methylmorpholine N-oxide monohydrate (NMO), OsO₄, H₂O / acetone; propan-2-ol / 15 h / Ambient temperature

5: Py / CH₂Cl₂ / 3 h / Ambient temperature

6: CH₂Cl₂ / 1.5 h / Ambient temperature

7: ethane-1,2-diol; CH₂Cl₂ / 14.5 h / Heating

8: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, 0 deg C 0.5 h, 2.) THF, RT, 4 h

9: 84 percent / TsOH / acetone; H₂O / 2.5 h / Heating

10: 84 percent / Et₃N / CH₂Cl₂; H₂O / 4 h / -78 °C / Heating

11: 1.) 3,3-dimethyldioxirane, 2.) camphorosulfonic acid / 1.) CH₂Cl₂, Me₂CO, 10 min, 2.) Me₂CO, 0.5 h

12: 97 percent / Pb(OAc)4 / benzene / 0.17 h / 0 °C

13: 97 percent / collidinium p-toluene sulfonate (CPTS) / 10 h / Heating

14: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

15: 88 percent / Bu₃P / tetrahydrofuran / 0.25 h / Ambient temperature

16: 90 percent / aq. H₂O₂ / tetrahydrofuran / 12 h / Ambient temperature

17: 1.) O₃, NaHCO₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 0.5 h

18: 1.) tBuLi, 3.) tetrabutylammonium fluoride

19: 80 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 11 h / Ambient temperature

20: 65 percent / H₂ / Pd/C / ethanol / 1.25 h / -5 °C

21: 81 percent / NaH / dimethylformamide

22: 93 percent / L-selectride / tetrahydrofuran / 1.25 h / -78 °C

23: 98 percent / KHMDS / tetrahydrofuran / 0.17 h / -78 °C

24: 96 percent / aq. pyridinium p-toluenesulfonate / acetone / 9 h / 75 °C

25: 77 percent / tetrahydrofuran / 0.42 h / -78 - 0 °C

26: 46 percent / Pd(Ph₃P)4, K₂CO₃, molecular sieves 4A / acetonitrile / 16.5 h / 90 °C

27: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

28: 92 percent / Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

29: 45 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 10.25 h / Ambient temperature

30: 82 percent / H₂, Pd(OAc)2 / ethanol / 10 h

31: 66 percent / Py, DMAP / 16 h / Ambient temperature

32: 93 percent / tetrahydrofuran; diethyl ether / 0.03 h / -78 °C

33: 1.) OsO₄, Py, 2.) Pb(OAc)4 / 1.) 105 deg C, 2.) C₆H₆, MeOH, 0 deg C, 5 min

34: 92 percent / SmI₂, Ac₂O / tetrahydrofuran / 0.17 h / -78 °C

35: 1.) KOtBu, 2.) (PhSeO)2O, 3.) KOtBu

With pyridine; lead(IV) acetate; dmap; palladium diacetate; palladium dihydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; samarium diiodide; tributylphosphine; collidinium p-toluene sulfonate; (PhSeO)2O; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; tert.-butyl lithium; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; acetic anhydride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; L-Selectride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; isopropyl alcohol; acetone; acetonitrile; benzene;
DOI:10.1021/ja952692a

Reference yield:

: 155681-63-3
tert-Butyl-dimethyl-((4'aS,5'S)-4'a-methyl-3',4',4'a,5',6',7'-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-yloxy)-silane

: 168421-82-7
C₃₅H₅₀O₉Si

Guidance literature:: Multi-step reaction with 36 steps

1: 1.) BH₃*THF, 2.) aq. H₂O₂, aq. NaOH, 3.) pyridinium dichromate

2: 1.) KHMDS / 1.) THF, -78 deg C, 2.) THF

3: 73 percent / Pd(OH)2, Ph₃P, Hunig's base / dimethylformamide

4: 99 percent / DIBAL / hexane / -78 °C

5: 45 percent / N-methylmorpholine N-oxide monohydrate (NMO), OsO₄, H₂O / acetone; propan-2-ol / 15 h / Ambient temperature

6: Py / CH₂Cl₂ / 3 h / Ambient temperature

7: CH₂Cl₂ / 1.5 h / Ambient temperature

8: ethane-1,2-diol; CH₂Cl₂ / 14.5 h / Heating

9: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, 0 deg C 0.5 h, 2.) THF, RT, 4 h

10: 84 percent / TsOH / acetone; H₂O / 2.5 h / Heating

11: 84 percent / Et₃N / CH₂Cl₂; H₂O / 4 h / -78 °C / Heating

12: 1.) 3,3-dimethyldioxirane, 2.) camphorosulfonic acid / 1.) CH₂Cl₂, Me₂CO, 10 min, 2.) Me₂CO, 0.5 h

13: 97 percent / Pb(OAc)4 / benzene / 0.17 h / 0 °C

14: 97 percent / collidinium p-toluene sulfonate (CPTS) / 10 h / Heating

15: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

16: 88 percent / Bu₃P / tetrahydrofuran / 0.25 h / Ambient temperature

17: 90 percent / aq. H₂O₂ / tetrahydrofuran / 12 h / Ambient temperature

18: 1.) O₃, NaHCO₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 0.5 h

19: 1.) tBuLi, 3.) tetrabutylammonium fluoride

20: 80 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 11 h / Ambient temperature

21: 65 percent / H₂ / Pd/C / ethanol / 1.25 h / -5 °C

22: 81 percent / NaH / dimethylformamide

23: 93 percent / L-selectride / tetrahydrofuran / 1.25 h / -78 °C

24: 98 percent / KHMDS / tetrahydrofuran / 0.17 h / -78 °C

25: 96 percent / aq. pyridinium p-toluenesulfonate / acetone / 9 h / 75 °C

26: 77 percent / tetrahydrofuran / 0.42 h / -78 - 0 °C

27: 46 percent / Pd(Ph₃P)4, K₂CO₃, molecular sieves 4A / acetonitrile / 16.5 h / 90 °C

28: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

29: 92 percent / Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

30: 45 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 10.25 h / Ambient temperature

31: 82 percent / H₂, Pd(OAc)2 / ethanol / 10 h

32: 66 percent / Py, DMAP / 16 h / Ambient temperature

33: 93 percent / tetrahydrofuran; diethyl ether / 0.03 h / -78 °C

34: 1.) OsO₄, Py, 2.) Pb(OAc)4 / 1.) 105 deg C, 2.) C₆H₆, MeOH, 0 deg C, 5 min

35: 92 percent / SmI₂, Ac₂O / tetrahydrofuran / 0.17 h / -78 °C

36: 1.) KOtBu, 2.) (PhSeO)2O, 3.) KOtBu

With pyridine; lead(IV) acetate; dmap; palladium diacetate; palladium dihydroxide; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; samarium diiodide; borane-THF; tributylphosphine; collidinium p-toluene sulfonate; (PhSeO)2O; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; tert.-butyl lithium; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; acetic anhydride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; L-Selectride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; isopropyl alcohol; acetone; acetonitrile; benzene;
DOI:10.1021/ja952692a