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

Base Information

Chemical Name:(Z)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-4-triethylsilanyloxy-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one
CAS No.:188259-84-9
Molecular Formula:C₅₆H₈₃NO₅SSi₃
Molecular Weight:966.601
Hs Code.:

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

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

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

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

There total 1 articles about (Z)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-4-triethylsilanyloxy-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one 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:

: 188259-73-6
(3S,5R,6R,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-3-triethylsilanyloxy-5-triphenylsilanyloxy-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester

: 188259-84-9
(Z)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-4-triethylsilanyloxy-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one

: (E)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-4-triethylsilanyloxy-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one

Guidance literature:: RuBnCl₂(PCy₃)2; In benzene; at 20 ℃; for 4h;
DOI:10.1021/ja971946k

Reference yield:

: 188259-84-9
(Z)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-4-triethylsilanyloxy-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one

: 152044-53-6
epithilone A

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / HF*pyridine / tetrahydrofuran / 20 °C

2: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -30 °C

3: 84 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 25 °C

4: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C

5: 49 percent / 3,3-dimethyldioxirane / CH₂Cl₂; acetone / 2 h / -50 - -30 °C

With 2,6-dimethylpyridine; 3,3-dimethyldioxirane; Dess-Martin periodane; pyridine hydrogenfluoride; In tetrahydrofuran; dichloromethane; acetone; 1: desilylation / 2: silylation / 3: Oxidation / 4: desilylation / 5: Epoxidation;
DOI:10.1021/ja971946k

Reference yield:

: 188259-84-9
(Z)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-4-triethylsilanyloxy-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one

: 186692-73-9
desoxyepothilone A

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / HF*pyridine / tetrahydrofuran / 20 °C

2: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -30 °C

3: 84 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 25 °C

4: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C

With 2,6-dimethylpyridine; Dess-Martin periodane; pyridine hydrogenfluoride; In tetrahydrofuran; dichloromethane; 1: desilylation / 2: silylation / 3: Oxidation / 4: desilylation;
DOI:10.1021/ja971946k