(R)-4-benzyl-3-[(2R,3S)-(E)-3-hydroxy-5-(2'-isopropyl[2,4']bithiazolyl-4-yl)-2-methylpent-4-enoyl]oxazolidin-2-one

Base Information

Chemical Name:(R)-4-benzyl-3-[(2R,3S)-(E)-3-hydroxy-5-(2'-isopropyl[2,4']bithiazolyl-4-yl)-2-methylpent-4-enoyl]oxazolidin-2-one
CAS No.:390386-36-4
Molecular Formula:C₂₅H₂₇N₃O₄S₂
Molecular Weight:497.639
Hs Code.:

Synonyms:(R)-4-benzyl-3-[(2R,3S)-(E)-3-hydroxy-5-(2'-isopropyl[2,4']bithiazolyl-4-yl)-2-methylpent-4-enoyl]oxazolidin-2-one

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Chemical Property of (R)-4-benzyl-3-[(2R,3S)-(E)-3-hydroxy-5-(2'-isopropyl[2,4']bithiazolyl-4-yl)-2-methylpent-4-enoyl]oxazolidin-2-one

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Technology Process of (R)-4-benzyl-3-[(2R,3S)-(E)-3-hydroxy-5-(2'-isopropyl[2,4']bithiazolyl-4-yl)-2-methylpent-4-enoyl]oxazolidin-2-one

There total 10 articles about (R)-4-benzyl-3-[(2R,3S)-(E)-3-hydroxy-5-(2'-isopropyl[2,4']bithiazolyl-4-yl)-2-methylpent-4-enoyl]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: 72.0%

: 101711-78-8,131685-53-5
(3R)-3-propionyl-4-benzyloxazolidin-2-one

: 390386-33-1
(E)-3-(2-(2-isopropylthiazol-4-yl)thiazol-4-yl)acrylaldehyde

: 390386-36-4
(R)-4-benzyl-3-[(2R,3S)-(E)-3-hydroxy-5-(2'-isopropyl[2,4']bithiazolyl-4-yl)-2-methylpent-4-enoyl]oxazolidin-2-one

Guidance literature:: (3R)-3-propionyl-4-benzyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 5 ℃; for 0.75h;

(E)-3-(2-(2-isopropylthiazol-4-yl)thiazol-4-yl)acrylaldehyde; In dichloromethane; at -78 - 0 ℃; for 3h;

With dihydrogen peroxide; In methanol; dichloromethane; at 0 - 10 ℃; for 1h; Further stages.;
DOI:10.1002/1521-3765(20021216)8:24<5585::AID-CHEM5585>3.0.CO;2-1

Reference yield:

: 376585-96-5
2'-isopropyl-4-bromo-2,4'-bithiazole

: 390386-36-4
(R)-4-benzyl-3-[(2R,3S)-(E)-3-hydroxy-5-(2'-isopropyl[2,4']bithiazolyl-4-yl)-2-methylpent-4-enoyl]oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 97 percent / Et₃N / [PdCl₂(PPh₃)2] / dioxane / 16 h / 100 °C

2.1: di-n-butylboron triflate; i-Pr₂NEt / CH₂Cl₂ / 0.75 h / 0 - 5 °C

2.2: CH₂Cl₂ / 3 h / -78 - 0 °C

2.3: 72 percent / aq. H₂O₂ / methanol; CH₂Cl₂ / 1 h / 0 - 10 °C

With di-n-butylboryl trifluoromethanesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; dichloromethane; 1.1: Stille cross-coupling reaction;
DOI:10.1002/1521-3765(20021216)8:24<5585::AID-CHEM5585>3.0.CO;2-1

Reference yield:

: 6620-69-5
2-isopropyl-4,5-dihydro-thiazole-4-carboxylic acid ethyl ester

: 390386-36-4
(R)-4-benzyl-3-[(2R,3S)-(E)-3-hydroxy-5-(2'-isopropyl[2,4']bithiazolyl-4-yl)-2-methylpent-4-enoyl]oxazolidin-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 9.1 g / DBU; BrCCl₃ / CH₂Cl₂ / 16 h / 20 °C

2.1: 87 percent / NH₃ gas / methanol / 15 h / 20 °C

3.1: Lawesson's reagent / xylene / 2 h / Heating

4.1: 4.03 g / K₂CO₃ / ethanol / 0.75 h / Heating

5.1: 78 percent / DIBAL-H / CH₂Cl₂; hexane / 0.67 h / -78 °C

6.1: 90 percent / NaH / tetrahydrofuran / 0.5 h

7.1: 89 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C

8.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

9.1: n-Bu₂BOTf; Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

9.2: CH₂Cl₂ / -78 - 0 °C

9.3: 72 percent / aq. H₂O₂ / CH₂Cl₂; methanol; aq. phosphate buffer / 1 h / 0 °C / pH 7

With Lawessons reagent; oxalyl dichloride; Bromotrichloromethane; di-n-butylboryl trifluoromethanesulfonate; ammonia; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; xylene; 6.1: Horner-Emmons reaction / 8.1: Swern oxidation;
DOI:10.1021/jo0106905