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

Base Information

Chemical Name:(Z)-(4S,7R,8S,9S,16S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione
CAS No.:187283-49-4
Molecular Formula:C₃₂H₅₃NO₅SSi
Molecular Weight:591.928
Hs Code.:

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

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

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

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

There total 1 articles about (Z)-(4S,7R,8S,9S,16S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-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

: 187283-49-4
(Z)-(4S,7R,8S,9S,16S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

2: 90 percent / benzene / 1 h / 80 °C

3: 96 percent / diethyl ether; pentane / 0.5 h / -100 °C

4: DCC, DMAP / toluene / 12 h / 25 °C

5: 50 percent / RuCl₂(=CHPh)(PCy₃)2 / CH₂Cl₂ / 8 h / 25 °C

With dmap; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; Grubbs catalyst first generation; In diethyl ether; dichloromethane; toluene; pentane; benzene;
DOI:10.1002/anie.199701661

Reference yield: 98.0%

: 187283-49-4
(Z)-(4S,7R,8S,9S,16S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione

: 186692-73-9
desoxyepothilone A

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 4h;
DOI:10.1002/anie.199701661

Reference yield:

: 187283-49-4
(Z)-(4S,7R,8S,9S,16S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione

: 152044-53-6
epithilone A

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / HF*pyridine / tetrahydrofuran

2: 45 percent / 3,3-dimethyldioxirane

With 3,3-dimethyldioxirane; pyridine hydrogenfluoride; In tetrahydrofuran;
DOI:10.1002/1521-3773(20020415)41:8<1404::AID-ANIE1404>3.0.CO;2-G