(E)-(S)-2-Methyl-1-(2-methyl-thiazol-4-yl)-6-trimethylsilanyl-hex-1-en-5-yn-3-ol

Base Information

Chemical Name:(E)-(S)-2-Methyl-1-(2-methyl-thiazol-4-yl)-6-trimethylsilanyl-hex-1-en-5-yn-3-ol
CAS No.:262375-77-9
Molecular Formula:C₁₄H₂₁NOSSi
Molecular Weight:279.478
Hs Code.:

Synonyms:(E)-(S)-2-Methyl-1-(2-methyl-thiazol-4-yl)-6-trimethylsilanyl-hex-1-en-5-yn-3-ol

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Chemical Property of (E)-(S)-2-Methyl-1-(2-methyl-thiazol-4-yl)-6-trimethylsilanyl-hex-1-en-5-yn-3-ol

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Technology Process of (E)-(S)-2-Methyl-1-(2-methyl-thiazol-4-yl)-6-trimethylsilanyl-hex-1-en-5-yn-3-ol

There total 1 articles about (E)-(S)-2-Methyl-1-(2-methyl-thiazol-4-yl)-6-trimethylsilanyl-hex-1-en-5-yn-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

: 262375-77-9
(E)-(S)-2-Methyl-1-(2-methyl-thiazol-4-yl)-6-trimethylsilanyl-hex-1-en-5-yn-3-ol

Guidance literature:: Multi-step reaction with 11 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

With 1H-imidazole; tributylphosphine; Tributylphosphine oxide; sulfuric acid; water; 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; 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;
DOI:10.1002/(SICI)1521-3773(20000103)39:1<209::AID-ANIE209>3.0.CO;2-F

Reference yield:

: 262375-77-9
(E)-(S)-2-Methyl-1-(2-methyl-thiazol-4-yl)-6-trimethylsilanyl-hex-1-en-5-yn-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 4 steps

1: 90 percent / [Ti(O-i-Pr)4]; i-PrMgCl / diethyl ether / -78 - -50 °C

2: 65 percent / I₂ / CH₂Cl₂

3: 90 percent / NEt₃; DMAP / CH₂Cl₂

4: 50 percent / 9-BBN; K₃PO₄ / [PdCl₂(dppf)] / tetrahydrofuran; dimethylformamide; H₂O / 60 °C

With titanium(IV) isopropylate; dmap; potassium phosphate; 9-borabicyclo[3.3.1]nonane dimer; iodine; isopropylmagnesium chloride; triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 1: Reduction / 2: Iodination / 3: Acetylation / 4: Suzuki coupling;
DOI:10.1002/(SICI)1521-3773(20000103)39:1<209::AID-ANIE209>3.0.CO;2-F

Reference yield:

: 262375-77-9
(E)-(S)-2-Methyl-1-(2-methyl-thiazol-4-yl)-6-trimethylsilanyl-hex-1-en-5-yn-3-ol

: C₄₄H₇₁NO₈S₂Si₂

Guidance literature:: Multi-step reaction with 8 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 30 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 14 h / 0 - 25 °C / Inert atmosphere

3.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

3.2: -78 - 25 °C / Inert atmosphere

4.1: dichloromethane / -20 - 0 °C / Inert atmosphere

5.1: methanol; sodium hydrogencarbonate / dichloromethane / 0 °C / Inert atmosphere

6.1: 2,6-dimethylpyridine / dichloromethane / -78 °C / Inert atmosphere

7.1: methanol; pyridinium p-toluenesulfonate / dichloromethane / 2 h / Inert atmosphere; Cooling

8.1: dmap; triethylamine / dichloromethane / 0 - 25 °C / Inert atmosphere

With 2,6-dimethylpyridine; methanol; dmap; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 3.2: Aldol condensation;
DOI:10.1002/ejoc.201101306