(2R,3E)-2-hydroxy-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenenitrile

Base Information

Chemical Name:(2R,3E)-2-hydroxy-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenenitrile
CAS No.:262375-55-3
Molecular Formula:C₉H₁₀N₂OS
Molecular Weight:194.257
Hs Code.:

Synonyms:(2R,3E)-2-hydroxy-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenenitrile

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Chemical Property of (2R,3E)-2-hydroxy-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenenitrile

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Technology Process of (2R,3E)-2-hydroxy-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenenitrile

There total 1 articles about (2R,3E)-2-hydroxy-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenenitrile 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:

: 6436-59-5
ethyl 2-methylthiazole-4-carboxylate

: 262375-55-3
(2R,3E)-2-hydroxy-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenenitrile

Guidance literature:: Multi-step reaction with 4 steps

1: 70 percent / DIBAL-H / CH₂Cl₂ / -78 °C

2: 90 percent / benzene / Heating

3: Bu₃P(O); Et₂AlCl; (S)-3,3'-(Ph₂PO)2-1,1'-binaphthalene-2,2'-diol / CH₂Cl₂; hexane / 39 h / -40 °C

4: TFA / CH₂Cl₂; hexane / 1 h / 20 °C

With Tributylphosphine oxide; diethylaluminium chloride; diisobutylaluminium hydride; trifluoroacetic acid; 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-bis-diphenylphosphine oxide; In hexane; dichloromethane; benzene; 1: Reduction / 2: Condensation / 3: Addition / 4: Acidolysis;
DOI:10.1002/(SICI)1521-3773(20000103)39:1<209::AID-ANIE209>3.0.CO;2-F

Reference yield:

: 262375-55-3
(2R,3E)-2-hydroxy-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenenitrile

: 152044-54-7
epothilone B

Guidance literature:: Multi-step reaction with 13 steps

1.1: 83 percent / aq. HCl / 5 h / 90 °C

2.1: 99 percent / imidazole / dimethylformamide / 3 h / 20 °C

3.1: 94 percent / DIBAL / toluene / 1 h / -78 °C

4.1: 68 percent / tetrahydrofuran / -78 - 20 °C

5.1: Hg(OAc)2; water / tetrahydrofuran / 2.5 h

5.2: 60 percent / tetrabutylammonium iodide / tetrahydrofuran; H₂O / 2 h

6.1: 100 percent / HF-pyridine / tetrahydrofuran / 12 h / 20 °C

7.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 6 h / 20 °C

8.1: 9-BBN / tetrahydrofuran / 1.5 h / 28 °C / microwave irradiation

8.2: 37 percent / K₃PO₄*3H₂O; H₂O / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide / 1 h / 60 °C

9.1: 93 percent / aq. NaOH / methanol / 36 h / 50 °C

10.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C

10.2: 90 percent / DMAP / toluene; tetrahydrofuran / 1 h

11.1: 92 percent / HF*pyridine / tetrahydrofuran

12.1: 97 percent / 3,3-dimethyldioxirane / CH₂Cl₂ / -35 °C

With 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 2,4,6-trichlorobenzoyl chloride; mercury(II) diacetate; water; 3,3-dimethyldioxirane; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: Wittig reaction;
DOI:10.1021/ja002024b

Reference yield:

: 262375-55-3
(2R,3E)-2-hydroxy-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenenitrile

: 189453-10-9
epothilone D

Guidance literature:: Multi-step reaction with 12 steps

1.1: 83 percent / aq. HCl / 5 h / 90 °C

2.1: 99 percent / imidazole / dimethylformamide / 3 h / 20 °C

3.1: 94 percent / DIBAL / toluene / 1 h / -78 °C

4.1: 68 percent / tetrahydrofuran / -78 - 20 °C

5.1: Hg(OAc)2; water / tetrahydrofuran / 2.5 h

5.2: 60 percent / tetrabutylammonium iodide / tetrahydrofuran; H₂O / 2 h

6.1: 100 percent / HF-pyridine / tetrahydrofuran / 12 h / 20 °C

7.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 6 h / 20 °C

8.1: 9-BBN / tetrahydrofuran / 1.5 h / 28 °C / microwave irradiation

8.2: 37 percent / K₃PO₄*3H₂O; H₂O / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide / 1 h / 60 °C

9.1: 93 percent / aq. NaOH / methanol / 36 h / 50 °C

10.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C

10.2: 90 percent / DMAP / toluene; tetrahydrofuran / 1 h

11.1: 92 percent / HF*pyridine / tetrahydrofuran

With 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 2,4,6-trichlorobenzoyl chloride; mercury(II) diacetate; water; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: Wittig reaction;
DOI:10.1021/ja002024b