(4S,7R,8S,9S,16S)-4,8-bis-(tert-butyldimethylsilanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-vinyl]-(13Z)-1-oxacyclohexadec-13-ene-2,6-dione

Base Information

Chemical Name:(4S,7R,8S,9S,16S)-4,8-bis-(tert-butyldimethylsilanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-vinyl]-(13Z)-1-oxacyclohexadec-13-ene-2,6-dione
CAS No.:186692-84-2
Molecular Formula:C₃₈H₆₇NO₅SSi₂
Molecular Weight:706.191
Hs Code.:

(4S,7R,8S,9S,16S)-4,8-bis-(tert-butyldimethylsilanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-vinyl]-(13Z)-1-oxacyclohexadec-13-ene-2,6-dione

Synonyms:(4S,7R,8S,9S,16S)-4,8-bis-(tert-butyldimethylsilanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-vinyl]-(13Z)-1-oxacyclohexadec-13-ene-2,6-dione

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Chemical Property of (4S,7R,8S,9S,16S)-4,8-bis-(tert-butyldimethylsilanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-vinyl]-(13Z)-1-oxacyclohexadec-13-ene-2,6-dione

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (4S,7R,8S,9S,16S)-4,8-bis-(tert-butyldimethylsilanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-vinyl]-(13Z)-1-oxacyclohexadec-13-ene-2,6-dione

There total 1 articles about (4S,7R,8S,9S,16S)-4,8-bis-(tert-butyldimethylsilanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-vinyl]-(13Z)-1-oxacyclohexadec-13-ene-2,6-dione 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

: 186692-84-2
(4S,7R,8S,9S,16S)-4,8-bis-(tert-butyldimethylsilanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-vinyl]-(13Z)-1-oxacyclohexadec-13-ene-2,6-dione

Guidance literature:: Multi-step reaction with 17 steps

1.1: 70 percent / DIBAL-H / CH₂Cl₂ / -78 °C

2.1: 90 percent / benzene / Heating

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

4.1: TFA / CH₂Cl₂; hexane / 1 h / 20 °C

5.1: 75 percent / H₂SO₄ / Heating

6.1: 99 percent / imidazole / dimethylformamide

7.1: 87 percent / DIBAL-H / toluene / -78 °C

8.1: tetrahydrofuran / -78 °C

9.1: tetrahydrofuran

10.1: 51 percent / HCO₂NH₄; Bu₃P / Pd(OAc)2 / benzene / 50 °C

11.1: 89 percent / AcOH; H₂O / tetrahydrofuran / 50 °C

12.1: 90 percent / [Ti(O-i-Pr)4]; i-PrMgCl / diethyl ether / -78 - -50 °C

13.1: 65 percent / I₂ / CH₂Cl₂

14.1: 90 percent / NEt₃; DMAP / CH₂Cl₂

15.1: 50 percent / 9-BBN; K₃PO₄ / [PdCl₂(dppf)] / tetrahydrofuran; dimethylformamide; H₂O / 60 °C

16.1: 84 percent / NaOH; H₂O / methanol

17.1: 2,4,6-trichlorobenzoyl chloride; NEt₃ / tetrahydrofuran

17.2: 88 percent / DMAP / toluene; tetrahydrofuran

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium hydroxide; potassium phosphate; 9-borabicyclo[3.3.1]nonane dimer; tributylphosphine; Tributylphosphine oxide; sulfuric acid; 2,4,6-trichlorobenzoyl chloride; 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; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 1.1: Reduction / 2.1: Condensation / 3.1: Addition / 4.1: Acidolysis / 5.1: Addition / 6.1: Etherification / 7.1: Reduction / 8.1: Addition / 9.1: Esterification / 10.1: Reductive deoxygenation / 11.1: Hydrolysis / 12.1: Reduction / 13.1: Iodination / 14.1: Acetylation / 15.1: Suzuki coupling / 16.1: Hydrolysis / 17.1: Esterification / 17.2: Cyclization;
DOI:10.1002/(SICI)1521-3773(20000103)39:1<209::AID-ANIE209>3.0.CO;2-F

Reference yield: 99.0%

: 186692-84-2
(4S,7R,8S,9S,16S)-4,8-bis-(tert-butyldimethylsilanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-vinyl]-(13Z)-1-oxacyclohexadec-13-ene-2,6-dione

: 186692-73-9
desoxyepothilone A

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; Ambient temperature;

Reference yield:

: 186692-84-2
(4S,7R,8S,9S,16S)-4,8-bis-(tert-butyldimethylsilanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-vinyl]-(13Z)-1-oxacyclohexadec-13-ene-2,6-dione

: 152044-53-6
epithilone A

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / TFA / CH₂Cl₂ / 1 h / 0 °C

2: 56 percent / methyl(trifluoromethyl)dioxirane / acetonitrile / 0 °C

With methyltrifluoromethyldioxirane; trifluoroacetic acid; In dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(01)01585-4