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

Base Information

Chemical Name:(Z)-(4R,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one
CAS No.:189453-47-2
Molecular Formula:C₅₁H₇₁NO₅SSi₂
Molecular Weight:866.365
Hs Code.:

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

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

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

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

There total 28 articles about (Z)-(4R,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-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:

: 189453-30-3
Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-(tert-butyl-dimethyl-silanyloxy)-4,8,10,12,12-pentamethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-13-oxo-11-triphenylsilanyloxy-tridec-3-enyl ester

: 189453-47-2
(Z)-(4R,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one

: 189453-43-8
(Z)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; Yield given. Yields of byproduct given;
DOI:10.1002/anie.199707571

Reference yield:

: 187283-46-1
(S,E)-2-methyl-1-(2-methylthiazol-4-yl)hexa-1,5-dien-3-ol

: 189453-47-2
(Z)-(4R,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 96 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 2 h

2.1: N-methylmorpholine N-oxide; water / OsO₄ / acetone; butan-1-ol / 2 h / 0 °C

3.1: NaIO₄ / tetrahydrofuran; H₂O / 1.25 h / 20 °C

4.1: 0.141 g / tetrahydrofuran; hexane / 0.67 h / -20 °C

5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 5 h / 20 °C

5.2: 77 percent / Cs₂CO₃; Ph₃As; H₂O / PdCl₂(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 3 h / 20 °C

6.1: 71 percent / pTSA*H₂O / dioxane; H₂O / 3 h / 55 °C

7.1: 0.055 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

With dmap; sodium periodate; water; potassium hexamethylsilazane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; acetone; toluene; butan-1-ol; 1.1: Acetylation / 2.1: Oxidation / 3.1: Oxidation / 4.1: Wittig reaction / 5.1: hydroboration / 5.2: Suzuki coupling / 6.1: Hydrolysis / 7.1: Cyclization;
DOI:10.1021/ja971946k

Reference yield:

: 188259-62-3
(1S)-[(1E)-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethynyl]-3-butenyl acetate

: 189453-47-2
(Z)-(4R,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: N-methylmorpholine N-oxide; water / OsO₄ / acetone; butan-1-ol / 2 h / 0 °C

2.1: NaIO₄ / tetrahydrofuran; H₂O / 1.25 h / 20 °C

3.1: 0.141 g / tetrahydrofuran; hexane / 0.67 h / -20 °C

4.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 5 h / 20 °C

4.2: 77 percent / Cs₂CO₃; Ph₃As; H₂O / PdCl₂(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 3 h / 20 °C

5.1: 71 percent / pTSA*H₂O / dioxane; H₂O / 3 h / 55 °C

6.1: 0.055 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

With sodium periodate; water; potassium hexamethylsilazane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 9-bora-bicyclo[3.3.1]nonane; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; hexane; water; acetone; toluene; butan-1-ol; 1.1: Oxidation / 2.1: Oxidation / 3.1: Wittig reaction / 4.1: hydroboration / 4.2: Suzuki coupling / 5.1: Hydrolysis / 6.1: Cyclization;
DOI:10.1021/ja971946k