(+)-(4R,5S)-3-{E-(2R,3S)-5-[2'-(E-2,E-4-(S)-1,6-dimethyl-hepta-2,4-dienyl)-[2,4']-bithiazolyl-4-yl]-3-hydroxy-2-methyl-pent-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one

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Chemical Name:(+)-(4R,5S)-3-{E-(2R,3S)-5-[2'-(E-2,E-4-(S)-1,6-dimethyl-hepta-2,4-dienyl)-[2,4']-bithiazolyl-4-yl]-3-hydroxy-2-methyl-pent-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one
CAS No.:910131-55-4
Molecular Formula:C₃₁H₃₅N₃O₄S₂
Molecular Weight:577.769
Hs Code.:

Synonyms:(+)-(4R,5S)-3-{E-(2R,3S)-5-[2'-(E-2,E-4-(S)-1,6-dimethyl-hepta-2,4-dienyl)-[2,4']-bithiazolyl-4-yl]-3-hydroxy-2-methyl-pent-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one

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Chemical Property of (+)-(4R,5S)-3-{E-(2R,3S)-5-[2'-(E-2,E-4-(S)-1,6-dimethyl-hepta-2,4-dienyl)-[2,4']-bithiazolyl-4-yl]-3-hydroxy-2-methyl-pent-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one

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Technology Process of (+)-(4R,5S)-3-{E-(2R,3S)-5-[2'-(E-2,E-4-(S)-1,6-dimethyl-hepta-2,4-dienyl)-[2,4']-bithiazolyl-4-yl]-3-hydroxy-2-methyl-pent-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one

There total 20 articles about (+)-(4R,5S)-3-{E-(2R,3S)-5-[2'-(E-2,E-4-(S)-1,6-dimethyl-hepta-2,4-dienyl)-[2,4']-bithiazolyl-4-yl]-3-hydroxy-2-methyl-pent-4-enoyl}-4-methyl-5-phenyl-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: 93.0%

: 910131-75-8
(+)-E-3-[2'-(E-2,E-4-(S)-1,6-dimethyl-hepta-2,4-dienyl)-[2,4']bithiazolyl-4-yl]propenal

: 77877-20-4
(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

: 910131-55-4
(+)-(4R,5S)-3-{E-(2R,3S)-5-[2'-(E-2,E-4-(S)-1,6-dimethyl-hepta-2,4-dienyl)-[2,4']-bithiazolyl-4-yl]-3-hydroxy-2-methyl-pent-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: (4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.25h;

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

(+)-E-3-[2'-(E-2,E-4-(S)-1,6-dimethyl-hepta-2,4-dienyl)-[2,4']bithiazolyl-4-yl]propenal; In dichloromethane; at -78 - 0 ℃; for 17h; Further stages.;
DOI:10.1039/b603433k

Reference yield:

: 910131-62-3
2-(E-4-methylpent-2-ene-1-sulfyl)-benzothiazole

: 910131-55-4
(+)-(4R,5S)-3-{E-(2R,3S)-5-[2'-(E-2,E-4-(S)-1,6-dimethyl-hepta-2,4-dienyl)-[2,4']-bithiazolyl-4-yl]-3-hydroxy-2-methyl-pent-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: 91 percent / (NH₄)6Mo₇O₂₄*4H₂O; aq. H₂O₂ / ethanol / 16 h / 20 °C

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 75 percent / tetrahydrofuran / 4 h / -78 - 20 °C

3.1: TBAF / tetrahydrofuran

3.2: 405 mg / I₂ / diethyl ether / 1.25 h / Heating; UV-irradiation

4.1: 1.3 g / KHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

5.1: 61 percent / NaClO₂; NaH₂PH₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 1.5 h / 20 °C

6.1: DMF; oxalyl chloride / CH₂Cl₂ / 3 h / 20 °C

7.1: 1.5 g / NH₃ / diethyl ether

8.1: 87 percent / Lawesson's reagent / tetrahydrofuran / 0.17 h / Heating

9.1: KHCO₃ / tetrahydrofuran / 0.08 h / -20 °C

9.2: 59 percent / trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.42 h / -20 - 20 °C

10.1: 56 percent / diisobutylaluminium hydride / hexane; tetrahydrofuran / 2 h / -78 - 0 °C

11.1: 58 percent / pyridinium dichromate / CH₂Cl₂ / 12 h / 20 °C

12.1: 72 percent / benzene / 1 h / Heating

13.1: n-Bu₂BOTf / CH₂Cl₂ / 0.25 h / 0 °C

13.2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

13.3: 93 percent / CH₂Cl₂ / 17 h / -78 - 0 °C

With Lawessons reagent; ammonium heptamolybdate; sodium chlorite; dipyridinium dichromate; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; diisobutylaluminium hydride; potassium hydrogencarbonate; Dess-Martin periodane; N,N-dimethyl-formamide; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 2.2: Julia olefination / 12.1: Wittig reaction;
DOI:10.1039/b603433k

Reference yield:

: C₂₆H₃₆OSi

: 910131-55-4
(+)-(4R,5S)-3-{E-(2R,3S)-5-[2'-(E-2,E-4-(S)-1,6-dimethyl-hepta-2,4-dienyl)-[2,4']-bithiazolyl-4-yl]-3-hydroxy-2-methyl-pent-4-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: TBAF / tetrahydrofuran

1.2: 405 mg / I₂ / diethyl ether / 1.25 h / Heating; UV-irradiation

2.1: 1.3 g / KHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

3.1: 61 percent / NaClO₂; NaH₂PH₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 1.5 h / 20 °C

4.1: DMF; oxalyl chloride / CH₂Cl₂ / 3 h / 20 °C

5.1: 1.5 g / NH₃ / diethyl ether

6.1: 87 percent / Lawesson's reagent / tetrahydrofuran / 0.17 h / Heating

7.1: KHCO₃ / tetrahydrofuran / 0.08 h / -20 °C

7.2: 59 percent / trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.42 h / -20 - 20 °C

8.1: 56 percent / diisobutylaluminium hydride / hexane; tetrahydrofuran / 2 h / -78 - 0 °C

9.1: 58 percent / pyridinium dichromate / CH₂Cl₂ / 12 h / 20 °C

10.1: 72 percent / benzene / 1 h / Heating

11.1: n-Bu₂BOTf / CH₂Cl₂ / 0.25 h / 0 °C

11.2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

11.3: 93 percent / CH₂Cl₂ / 17 h / -78 - 0 °C

With Lawessons reagent; sodium chlorite; dipyridinium dichromate; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; ammonia; diisobutylaluminium hydride; potassium hydrogencarbonate; Dess-Martin periodane; N,N-dimethyl-formamide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 10.1: Wittig reaction;
DOI:10.1039/b603433k