Carbonic acid (E)-(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-4-(2-methyl-thiazol-4-yl)-1-trimethylsilanylethynyl-but-3-enyl ester methyl ester

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Chemical Name:Carbonic acid (E)-(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-4-(2-methyl-thiazol-4-yl)-1-trimethylsilanylethynyl-but-3-enyl ester methyl ester
CAS No.:262375-76-8
Molecular Formula:C₂₂H₃₇NO₄SSi₂
Molecular Weight:467.777
Hs Code.:

Carbonic acid (E)-(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-4-(2-methyl-thiazol-4-yl)-1-trimethylsilanylethynyl-but-3-enyl ester methyl ester

Synonyms:Carbonic acid (E)-(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-4-(2-methyl-thiazol-4-yl)-1-trimethylsilanylethynyl-but-3-enyl ester methyl ester

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Chemical Property of Carbonic acid (E)-(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-4-(2-methyl-thiazol-4-yl)-1-trimethylsilanylethynyl-but-3-enyl ester methyl ester

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Technology Process of Carbonic acid (E)-(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-4-(2-methyl-thiazol-4-yl)-1-trimethylsilanylethynyl-but-3-enyl ester methyl ester

There total 1 articles about Carbonic acid (E)-(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-4-(2-methyl-thiazol-4-yl)-1-trimethylsilanylethynyl-but-3-enyl ester methyl ester 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

: 262375-76-8
Carbonic acid (E)-(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-4-(2-methyl-thiazol-4-yl)-1-trimethylsilanylethynyl-but-3-enyl ester methyl ester

Guidance literature:: Multi-step reaction with 9 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

With 1H-imidazole; Tributylphosphine oxide; sulfuric acid; diethylaluminium chloride; diisobutylaluminium hydride; trifluoroacetic acid; 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-bis-diphenylphosphine oxide; 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;
DOI:10.1002/(SICI)1521-3773(20000103)39:1<209::AID-ANIE209>3.0.CO;2-F

Reference yield:

: 262375-76-8
Carbonic acid (E)-(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-4-(2-methyl-thiazol-4-yl)-1-trimethylsilanylethynyl-but-3-enyl ester methyl ester

: 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 5 steps

1.1: 51 percent / ammonium formate; tributylphosphine / Pd(OAc)2 / benzene / 24 h / 50 °C

2.1: 26 percent / Ti(O-i-Pr)4; i-PrMgCl / diethyl ether / 1 h / -50 °C

3.1: 59 percent / I₂ / CH₂Cl₂ / 12 h / 20 °C

4.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 6 h / 20 °C

5.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation

5.2: 50 percent / K₃PO₄*3H₂O; H₂O / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C

With titanium(IV) isopropylate; dmap; 9-borabicyclo[3.3.1]nonane dimer; tributylphosphine; iodine; isopropylmagnesium chloride; ammonium formate; triethylamine; palladium diacetate; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1021/ja002024b

Reference yield:

: 262375-76-8
Carbonic acid (E)-(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-4-(2-methyl-thiazol-4-yl)-1-trimethylsilanylethynyl-but-3-enyl ester methyl ester

: 152044-53-6
epithilone A

Guidance literature:: Multi-step reaction with 9 steps

1.1: 51 percent / ammonium formate; tributylphosphine / Pd(OAc)2 / benzene / 24 h / 50 °C

2.1: 26 percent / Ti(O-i-Pr)4; i-PrMgCl / diethyl ether / 1 h / -50 °C

3.1: 59 percent / I₂ / CH₂Cl₂ / 12 h / 20 °C

4.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 6 h / 20 °C

5.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation

5.2: 50 percent / K₃PO₄*3H₂O; H₂O / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C

6.1: 84 percent / aq. NaOH / methanol / 36 h / 50 °C

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

7.2: 88 percent / DMAP / toluene; tetrahydrofuran / 1 h

8.1: 99 percent / HF*pyridine / tetrahydrofuran

9.1: 49 percent / 3,3-dimethyldioxirane / CH₂Cl₂ / -35 °C

With titanium(IV) isopropylate; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; tributylphosphine; 2,4,6-trichlorobenzoyl chloride; iodine; isopropylmagnesium chloride; ammonium formate; 3,3-dimethyldioxirane; pyridine hydrogenfluoride; triethylamine; palladium diacetate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;
DOI:10.1021/ja002024b