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

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Chemical Name:(Z)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one
CAS No.:186692-71-7
Molecular Formula:C₅₀H₆₉NO₅SSi₂
Molecular Weight:852.339
Hs Code.:

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

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

There total 46 articles about (Z)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9-tetramethyl-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:

: 186692-59-1
2-[(2R,3R,4S,5S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1,1,3,5-tetramethyl-2-triphenylsilanyloxy-hexyl]-[1,3]dithiane

: 186692-71-7
(Z)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 20 °C

2.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

2.2: 90 percent / Et₃N / CH₂Cl₂ / -78 - 0 °C

3.1: 2.83 g / tetrahydrofuran / 2 h / 0 - 20 °C

4.1: 99 percent / pTSA*H₂O / dioxane; H₂O / 2 h / 50 °C

5.1: 76 percent / tetrahydrofuran / 1 h / 0 - 20 °C

6.1: 92 percent / [bis(trifluoroacetoxy)iodobenzene] / tetrahydrofuran / 0.25 h / 20 °C

7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C

7.2: 75 percent / Cs₂CO₃; Ph₃As; H₂O / PdCl₂(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C

8.1: 85 percent / pTSA*H₂O / dioxane; H₂O / 3 h / 55 °C

9.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C

With oxalyl dichloride; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; 9-bora-bicyclo[3.3.1]nonane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene; 1.1: Oxidation / 2.1: Condensation / 2.2: Elimination / 3.1: Wittig reaction / 4.1: Hydrolysis / 5.1: Wittig reaction / 6.1: Ring cleavage / 7.1: hydroboration / 7.2: Suzuki coupling / 8.1: Hydrolysis / 9.1: Cyclization;
DOI:10.1021/ja971946k

Reference yield:

: 186692-74-0
(2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[1,3]dithian-2-yl-2,4,6-trimethyl-5-triphenylsilanyloxy-heptan-1-ol

: 186692-71-7
(Z)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

1.2: 90 percent / Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: 2.83 g / tetrahydrofuran / 2 h / 0 - 20 °C

3.1: 99 percent / pTSA*H₂O / dioxane; H₂O / 2 h / 50 °C

4.1: 76 percent / tetrahydrofuran / 1 h / 0 - 20 °C

5.1: 92 percent / [bis(trifluoroacetoxy)iodobenzene] / tetrahydrofuran / 0.25 h / 20 °C

6.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C

6.2: 75 percent / Cs₂CO₃; Ph₃As; H₂O / PdCl₂(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C

7.1: 85 percent / pTSA*H₂O / dioxane; H₂O / 3 h / 55 °C

8.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C

With oxalyl dichloride; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; 9-bora-bicyclo[3.3.1]nonane; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene; 1.1: Condensation / 1.2: Elimination / 2.1: Wittig reaction / 3.1: Hydrolysis / 4.1: Wittig reaction / 5.1: Ring cleavage / 6.1: hydroboration / 6.2: Suzuki coupling / 7.1: Hydrolysis / 8.1: Cyclization;
DOI:10.1021/ja971946k

Reference yield:

: 184297-54-9
(2S,3S,4R,5R)-1-Benzyloxy-6-[1,3]dithian-2-yl-2,4,6-trimethyl-5-triphenylsilanyloxy-heptan-3-ol

: 186692-71-7
(Z)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

2.1: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 20 °C

3.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

3.2: 90 percent / Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: 2.83 g / tetrahydrofuran / 2 h / 0 - 20 °C

5.1: 99 percent / pTSA*H₂O / dioxane; H₂O / 2 h / 50 °C

6.1: 76 percent / tetrahydrofuran / 1 h / 0 - 20 °C

7.1: 92 percent / [bis(trifluoroacetoxy)iodobenzene] / tetrahydrofuran / 0.25 h / 20 °C

8.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C

8.2: 75 percent / Cs₂CO₃; Ph₃As; H₂O / PdCl₂(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C

9.1: 85 percent / pTSA*H₂O / dioxane; H₂O / 3 h / 55 °C

10.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C

With 2,6-dimethylpyridine; oxalyl dichloride; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; 9-bora-bicyclo[3.3.1]nonane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene; 1.1: silylation / 2.1: Oxidation / 3.1: Condensation / 3.2: Elimination / 4.1: Wittig reaction / 5.1: Hydrolysis / 6.1: Wittig reaction / 7.1: Ring cleavage / 8.1: hydroboration / 8.2: Suzuki coupling / 9.1: Hydrolysis / 10.1: Cyclization;
DOI:10.1021/ja971946k