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

Base Information

Chemical Name:(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-yl acetate
CAS No.:186692-68-2
Molecular Formula:C₁₃H₁₆INO₂S
Molecular Weight:377.246
Hs Code.:

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

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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-yl acetate

Chemical Property:

Purity/Quality:

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MSDS Files:: SDS file from LookChem

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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-yl acetate

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

: 186692-68-2
(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-yl acetate

Guidance literature:: Multi-step reaction with 14 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

14: 90 percent / NEt₃; DMAP / CH₂Cl₂

With 1H-imidazole; titanium(IV) isopropylate; dmap; tributylphosphine; Tributylphosphine oxide; sulfuric acid; water; iodine; isopropylmagnesium chloride; ammonium formate; diethylaluminium chloride; diisobutylaluminium hydride; acetic acid; triethylamine; 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 / 14: Acetylation;
DOI:10.1002/(SICI)1521-3773(20000103)39:1<209::AID-ANIE209>3.0.CO;2-F

Reference yield: 75.0%

: 186692-68-2
(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-yl acetate

: 186692-63-7
C₃₉H₅₈O₄Si₂

: 186692-69-3
Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-(tert-butyl-dimethyl-silanyloxy)-13,13-dimethoxy-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-11-triphenylsilanyloxy-tridec-3-enyl ester

Guidance literature:: C₃₉H₅₈O₄Si₂; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 20 ℃; for 4h;

(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-yl acetate; With triphenyl-arsane; water; caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 2h;
DOI:10.1021/ja971946k

Reference yield: 60.0%

: 186692-68-2
(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-yl acetate

: 297131-72-7
{(1S,2S)-1-[(1R,2R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,3-trimethyl-butyl]-2-methyl-pent-4-enyloxymethyl}-benzene

: 297131-79-4
Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-benzyloxy-11,13-bis-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-tridec-3-enyl ester

Guidance literature:: {(1S,2S)-1-[(1R,2R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,3-trimethyl-butyl]-2-methyl-pent-4-enyloxymethyl}-benzene; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 20 ℃; for 4h;

(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-yl acetate; With triphenyl-arsane; caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water; for 1.5h;
DOI:10.1002/1099-0690(200105)2001:9<1701::AID-EJOC1701>3.0.CO;2-#