(E)-(R)-5-Bromo-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-3-triisopropylsilanyloxy-hex-4-en-1-one

Base Information

Chemical Name:(E)-(R)-5-Bromo-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-3-triisopropylsilanyloxy-hex-4-en-1-one
CAS No.:218782-65-1
Molecular Formula:C₂₁H₃₈BrNO₂S₂Si
Molecular Weight:508.66
Hs Code.:

Synonyms:(E)-(R)-5-Bromo-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-3-triisopropylsilanyloxy-hex-4-en-1-one

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Chemical Property of (E)-(R)-5-Bromo-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-3-triisopropylsilanyloxy-hex-4-en-1-one

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Technology Process of (E)-(R)-5-Bromo-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-3-triisopropylsilanyloxy-hex-4-en-1-one

There total 1 articles about (E)-(R)-5-Bromo-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-3-triisopropylsilanyloxy-hex-4-en-1-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: 99.0%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 218782-63-9
(E)-(R)-5-Bromo-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-hex-4-en-1-one

: 218782-65-1
(E)-(R)-5-Bromo-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-3-triisopropylsilanyloxy-hex-4-en-1-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃;
DOI:10.1021/ja973549f

Reference yield:

: 218782-65-1
(E)-(R)-5-Bromo-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-3-triisopropylsilanyloxy-hex-4-en-1-one

: 139220-18-1
(-)-pateamine

Guidance literature:: Multi-step reaction with 21 steps

1: 90 percent / NH₃ gas / CH₂Cl₂ / 0 °C

2: 72 percent / (PhOPh)2P₂S₄ / tetrahydrofuran / 0.5 h / 25 °C

3: KHCO₃ / 1,2-dimethoxy-ethane / -30 - 25 °C

4: trifluoroacetic anhydride, 2,6-lutidine / 1,2-dimethoxy-ethane / 1 h / -30 °C

5: 80 percent / DIBAL-H / CH₂Cl₂ / 3 h / -90 °C

6: 1.) NaHMDS / 1.) THF, 25 deg C, 15 min, 2.) THF, 25 deg C, 1.5 h

7: 1.) CuBr*DMS / 1.) THF, Et₂O, from -78 to 0 deg C, 30 min, 2.) THF, Et₂O, CH₂Cl₂, -30 deg C, 3.5 h

8: 1.) AlMe₃ / 1.) CH₂Cl₂, toluene, 25 deg C, 30 min, 2.) CH₂Cl₂, toluene, -20 deg C, 8 h

9: 95 percent / DIBAL-H / tetrahydrofuran; CH₂Cl₂ / 1.3 h / -78 °C

10: 1.) Sn(OTf)2, N-ethylpiperidine / 1.) CH₂Cl₂, -50 deg C, 4 h, 2.) CH₂Cl₂, -78 deg C, 1 h

11: 1.) Et₃N / 1.) CH₂Cl₂, 25 deg C, 30 min, 2.) CH₂Cl₂, RT, 27 h

12: 92 percent / diisopropylazodicarboxylate, Ph₃P / tetrahydrofuran / 2.5 h / 25 °C

13: 96 percent / aq. SmI₂ / tetrahydrofuran / 1 h / 0 °C

14: 51 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / 25 °C

15: 78 percent / TBAF, AcOH / tetrahydrofuran / 1 h / -20 °C

16: 57 percent / DIAD, Ph₃P / tetrahydrofuran / 1.5 h / -20 °C

17: 78 percent / HF, pyridine / tetrahydrofuran / 5 h / 25 °C

18: 68 percent / Et₄NCN / CH₂Cl₂ / 6 h / 25 °C

19: H₂ / Pd/CaCO₃ poisoned with Pb / methanol / 17 h / 25 °C / 760 Torr

20: 27 percent / Pd₂dba3*CHCl₃, triphenyl arsine / tetrahydrofuran / 33 h / 25 °C

21: 78 percent / NH₄OAc, Cd-Pb / tetrahydrofuran / 3.5 h / 25 °C

With 1-ethyl-piperidine; pyridine; 2,6-dimethylpyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 10% Cd/Pd; tin(II) trifluoromethanesulfonate; samarium diiodide; copper(I) bromide dimethylsulfide complex; triphenyl-arsane; di-isopropyl azodicarboxylate; (PhOPh)2P₂S₄; hydrogen fluoride; ammonium acetate; tetraethylammoniumcyanide; tetrabutyl ammonium fluoride; ammonia; hydrogen; trimethylaluminum; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; acetic acid; triethylamine; triphenylphosphine; trifluoroacetic anhydride; Lindlar's catalyst; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/ja981846u

Reference yield:

: 218782-65-1
(E)-(R)-5-Bromo-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-3-triisopropylsilanyloxy-hex-4-en-1-one

: 201340-05-8
(R)-1-Benzyloxy-4-{(S)-2-[2-((E)-(R)-4-bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-propyl}-azetidin-2-one

Guidance literature:: Multi-step reaction with 12 steps

1: 90 percent / NH₃ gas / CH₂Cl₂ / 0 °C

2: 72 percent / (PhOPh)2P₂S₄ / tetrahydrofuran / 0.5 h / 25 °C

3: KHCO₃ / 1,2-dimethoxy-ethane / -30 - 25 °C

4: trifluoroacetic anhydride, 2,6-lutidine / 1,2-dimethoxy-ethane / 1 h / -30 °C

5: 80 percent / DIBAL-H / CH₂Cl₂ / 3 h / -90 °C

6: 1.) NaHMDS / 1.) THF, 25 deg C, 15 min, 2.) THF, 25 deg C, 1.5 h

7: 1.) CuBr*DMS / 1.) THF, Et₂O, from -78 to 0 deg C, 30 min, 2.) THF, Et₂O, CH₂Cl₂, -30 deg C, 3.5 h

8: 1.) AlMe₃ / 1.) CH₂Cl₂, toluene, 25 deg C, 30 min, 2.) CH₂Cl₂, toluene, -20 deg C, 8 h

9: 95 percent / DIBAL-H / tetrahydrofuran; CH₂Cl₂ / 1.3 h / -78 °C

10: 1.) Sn(OTf)2, N-ethylpiperidine / 1.) CH₂Cl₂, -50 deg C, 4 h, 2.) CH₂Cl₂, -78 deg C, 1 h

11: 1.) Et₃N / 1.) CH₂Cl₂, 25 deg C, 30 min, 2.) CH₂Cl₂, RT, 27 h

12: 92 percent / diisopropylazodicarboxylate, Ph₃P / tetrahydrofuran / 2.5 h / 25 °C

With 1-ethyl-piperidine; 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; copper(I) bromide dimethylsulfide complex; di-isopropyl azodicarboxylate; (PhOPh)2P₂S₄; ammonia; trimethylaluminum; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; triethylamine; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/ja981846u