(S)-4-Benzyl-3-((1R,2R,3R,4R,7R)-3-chloro-7-dimethylsilanyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Benzyl-3-((1R,2R,3R,4R,7R)-3-chloro-7-dimethylsilanyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one
• CAS No.: 321172-23-0
• Molecular Formula: C₂₀H₂₄ClNO₃Si
• Molecular Weight: 389.954
• Mol file: 321172-23-0.mol

Synonyms:(S)-4-Benzyl-3-((1R,2R,3R,4R,7R)-3-chloro-7-dimethylsilanyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one

Chemical Property of (S)-4-Benzyl-3-((1R,2R,3R,4R,7R)-3-chloro-7-dimethylsilanyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-Benzyl-3-((1R,2R,3R,4R,7R)-3-chloro-7-dimethylsilanyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one

There total 1 articles about (S)-4-Benzyl-3-((1R,2R,3R,4R,7R)-3-chloro-7-dimethylsilanyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-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: 88.0%

cyclopentadienyldimethylsilane (83303-35-9) + (S)-4-Benzyl-3-((E)-3-chloro-acryloyl)-oxazolidin-2-one → (S)-4-Benzyl-3-((1R,2R,3R,4R,7R)-3-chloro-7-dimethylsilanyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one (321172-23-0)

Guidance literature:

With diethylaluminium chloride; In dichloromethane; at -78 ℃;

Reference yield:

(S)-4-Benzyl-3-((1R,2R,3R,4R,7R)-3-chloro-7-dimethylsilanyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one (321172-23-0) → gelsemine (509-15-9)

Guidance literature:

Multi-step reaction with 32 steps

1.1: 99 percent / Sm(OTf)3

2.1: 53 percent / aq. H₂O₂; KF; KHCO₃ / tetrahydrofuran; methanol

3.1: 100 percent / tBuOOH; VO(acac)2 / benzene

4.1: 97 percent / 2,6-lutidine / CH₂Cl₂

5.1: 98 percent / tBuOK / benzene

6.1: methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) / toluene / -20 °C

7.1: piperidine / methanol

8.1: 87 percent / TBAF / tetrahydrofuran

9.1: CrO₃; H₂SO₄ / acetone

10.1: toluene; acetonitrile / 90 °C

11.1: nBuLi / tetrahydrofuran / 65 °C

12.1: tBuOK

13.1: 75 percent / nBu₃SnH; AIBN / benzene / Heating

14.1: 100 percent / methanol

15.1: 94 percent / pyridine; DMAP / CH₂Cl₂

16.1: 94 percent / LiBH₄; LiBEt₃H / tetrahydrofuran

17.1: pyrrolidine / [Pd(PPh₃)4] / tetrahydrofuran

18.1: DIEA / acetonitrile / 60 °C

19.1: 62 percent / KHMDS / tetrahydrofuran / -78 - 0 °C

20.1: 92 percent / pyridine; DMAP / CH₂Cl₂

21.1: 96 percent / HCO₂H

22.1: NEt₃ / tetrahydrofuran

23.1: NaBH₄; H₂O / tetrahydrofuran

24.1: PBu₃ / tetrahydrofuran

25.1: MCPBA / tetrahydrofuran

26.1: NEt₃ / tetrahydrofuran

27.1: MCPBA / tetrahydrofuran; H₂O

28.1: NEt₃ / tetrahydrofuran

29.1: 96 percent / K₂CO₃; MeOH

30.1: Hg(OTf)2*PhNMe₂ / nitromethane

30.2: aq. NaCl

30.3: NaBH₄; aq. NaOH; BnNEt₃Cl / CH₂Cl₂

31.1: TMSCl; NaI / acetonitrile

31.2: 63 percent / NEt₃ / methanol

32.1: 90 percent / DIBAL / toluene

With pyrrolidine; piperidine; pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; methanol; tert.-butylhydroperoxide; dmap; potassium fluoride; sodium tetrahydroborate; lithium borohydride; n-butyllithium; chloro-trimethyl-silane; formic acid; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); tributylphosphine; Hg(OSO₂CF₃)2*C₆H₅N(CH₃)2; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; tri-n-butyl-tin hydride; potassium hexamethylsilazane; bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum; diisobutylaluminium hydride; lithium triethylborohydride; potassium carbonate; potassium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; samarium(III) trifluoromethanesulfonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; nitromethane; dichloromethane; water; acetone; toluene; acetonitrile; benzene; 9.1: Jones' oxidation / 11.1: Horner-Emmons reaction / 14.1: Michael addition / 19.1: Michael addition;

Reference yield:

(S)-4-Benzyl-3-((1R,2R,3R,4R,7R)-3-chloro-7-dimethylsilanyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one (321172-23-0) → C30H29N3O6 (321172-91-2)

Guidance literature:

Multi-step reaction with 21 steps

1: 99 percent / Sm(OTf)3

2: 53 percent / aq. H₂O₂; KF; KHCO₃ / tetrahydrofuran; methanol

3: 100 percent / tBuOOH; VO(acac)2 / benzene

4: 97 percent / 2,6-lutidine / CH₂Cl₂

5: 98 percent / tBuOK / benzene

6: methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) / toluene / -20 °C

7: piperidine / methanol

8: 87 percent / TBAF / tetrahydrofuran

9: CrO₃; H₂SO₄ / acetone

10: toluene; acetonitrile / 90 °C

11: nBuLi / tetrahydrofuran / 65 °C

12: tBuOK

13: 75 percent / nBu₃SnH; AIBN / benzene / Heating

14: 100 percent / methanol

15: 94 percent / pyridine; DMAP / CH₂Cl₂

16: 94 percent / LiBH₄; LiBEt₃H / tetrahydrofuran

17: pyrrolidine / [Pd(PPh₃)4] / tetrahydrofuran

18: DIEA / acetonitrile / 60 °C

19: 62 percent / KHMDS / tetrahydrofuran / -78 - 0 °C

20: 92 percent / pyridine; DMAP / CH₂Cl₂

21: 96 percent / HCO₂H

With pyrrolidine; piperidine; pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; tert.-butylhydroperoxide; dmap; potassium fluoride; lithium borohydride; n-butyllithium; formic acid; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; potassium hexamethylsilazane; bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum; lithium triethylborohydride; potassium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; samarium(III) trifluoromethanesulfonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; acetonitrile; benzene; 9: Jones' oxidation / 11: Horner-Emmons reaction / 14: Michael addition / 19: Michael addition;

upstream raw materials:

cyclopentadienyldimethylsilane

Downstream raw materials:

gelsemine

C₂₉H₂₈N₂O₅

C₃₀H₂₉N₃O₄

C₃₀H₃₁N₃O₅

Refernces