(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-ol

Base Information

Chemical Name:(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-ol
CAS No.:186692-81-9
Molecular Formula:C₁₁H₁₄INOS
Molecular Weight:335.209
Hs Code.:

Synonyms:(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-ol

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-ol

There total 1 articles about (1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-ol 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

: 186692-81-9
(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-ol

Guidance literature:: Multi-step reaction with 13 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

5: 75 percent / H₂SO₄ / Heating

6: 99 percent / imidazole / dimethylformamide

7: 87 percent / DIBAL-H / toluene / -78 °C

8: tetrahydrofuran / -78 °C

9: tetrahydrofuran

10: 51 percent / HCO₂NH₄; Bu₃P / Pd(OAc)2 / benzene / 50 °C

11: 89 percent / AcOH; H₂O / tetrahydrofuran / 50 °C

12: 90 percent / [Ti(O-i-Pr)4]; i-PrMgCl / diethyl ether / -78 - -50 °C

13: 65 percent / I₂ / CH₂Cl₂

With 1H-imidazole; titanium(IV) isopropylate; tributylphosphine; Tributylphosphine oxide; sulfuric acid; water; iodine; isopropylmagnesium chloride; ammonium formate; diethylaluminium chloride; diisobutylaluminium hydride; acetic acid; trifluoroacetic acid; 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-bis-diphenylphosphine oxide; palladium diacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1: Reduction / 2: Condensation / 3: Addition / 4: Acidolysis / 5: Addition / 6: Etherification / 7: Reduction / 8: Addition / 9: Esterification / 10: Reductive deoxygenation / 11: Hydrolysis / 12: Reduction / 13: Iodination;
DOI:10.1002/(SICI)1521-3773(20000103)39:1<209::AID-ANIE209>3.0.CO;2-F

Reference yield:

: 186692-81-9
(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-ol

: 312730-84-0
(3S,6R,7S,8S,12Z,15S,16E)-phenyl 3,7-di-tert-butyldimethylsilyloxy-15-methoxycarbonyl-4,4,6,8,16-pentamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 6 h / 20 °C

2.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation

2.2: 50 percent / K₃PO₄*3H₂O; H₂O / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C

With dmap; 9-borabicyclo[3.3.1]nonane dimer; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja002024b

Reference yield:

: 186692-81-9
(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-ol

: 186692-71-7
(Z)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99 percent / pyridine; 4-DMAP / CH₂Cl₂ / 20 °C

2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C

2.2: 75 percent / Cs₂CO₃; Ph₃As; H₂O / PdCl₂(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C

3.1: 85 percent / pTSA*H₂O / dioxane; H₂O / 3 h / 55 °C

4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C

With pyridine; dmap; potassium hexamethylsilazane; toluene-4-sulfonic acid; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene; 1.1: Acetylation / 2.1: hydroboration / 2.2: Suzuki coupling / 3.1: Hydrolysis / 4.1: Cyclization;
DOI:10.1021/ja971946k