(Z)-(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]-6-triphenylsilanyloxy-oxacyclohexadec-13-ene-2,4-dione

Base Information

Chemical Name:(Z)-(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]-6-triphenylsilanyloxy-oxacyclohexadec-13-ene-2,4-dione
CAS No.:197233-32-2
Molecular Formula:C₅₀H₆₇NO₅SSi₂
Molecular Weight:850.323
Hs Code.:

(Z)-(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]-6-triphenylsilanyloxy-oxacyclohexadec-13-ene-2,4-dione

Synonyms:(Z)-(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]-6-triphenylsilanyloxy-oxacyclohexadec-13-ene-2,4-dione

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Chemical Property of (Z)-(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]-6-triphenylsilanyloxy-oxacyclohexadec-13-ene-2,4-dione

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (Z)-(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]-6-triphenylsilanyloxy-oxacyclohexadec-13-ene-2,4-dione

There total 41 articles about (Z)-(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]-6-triphenylsilanyloxy-oxacyclohexadec-13-ene-2,4-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:

: 184246-38-6
(E)-2-methyl-3-(2-methylthiazol-4-yl)acrylaldehyde

: 197233-32-2
(Z)-(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]-6-triphenylsilanyloxy-oxacyclohexadec-13-ene-2,4-dione

Guidance literature:: Multi-step reaction with 9 steps

1.1: 60 percent / (S)-(-)-1,1'-bi-2-naphthol; Ti(O-i-Pr)4; 4 Angstroem sieves / CH₂Cl₂ / 70 h / -78 - -20 °C

2.1: 96 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 2 h

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

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

5.1: 0.014 g / HMPA / tetrahydrofuran / 0.5 h / -78 - 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

9.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

With titanium(IV) isopropylate; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium periodate; 4 A molecular sieve; water; (S)-[1,1']-binaphthalenyl-2,2'-diol; potassium hexamethylsilazane; Dess-Martin periodane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetone; toluene; butan-1-ol; 1.1: Addition / 2.1: Acetylation / 3.1: Oxidation / 4.1: Oxidation / 5.1: Wittig reaction / 6.1: hydroboration / 6.2: Suzuki coupling / 7.1: Hydrolysis / 8.1: Cyclization / 9.1: Oxidation;
DOI:10.1021/ja971946k

Reference yield:

: 20949-84-2
2-methylthiazole-4-carbaldehyde

: 197233-32-2
(Z)-(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]-6-triphenylsilanyloxy-oxacyclohexadec-13-ene-2,4-dione

Guidance literature:: Multi-step reaction with 10 steps

1.1: 83 percent / benzene / Heating

2.1: 60 percent / (S)-(-)-1,1'-bi-2-naphthol; Ti(O-i-Pr)4; 4 Angstroem sieves / CH₂Cl₂ / 70 h / -78 - -20 °C

3.1: 96 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 2 h

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

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

6.1: 0.014 g / HMPA / tetrahydrofuran / 0.5 h / -78 - 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

10.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

With titanium(IV) isopropylate; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium periodate; 4 A molecular sieve; water; (S)-[1,1']-binaphthalenyl-2,2'-diol; potassium hexamethylsilazane; Dess-Martin periodane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetone; toluene; butan-1-ol; benzene; 1.1: Wittig reaction / 2.1: Addition / 3.1: Acetylation / 4.1: Oxidation / 5.1: Oxidation / 6.1: Wittig reaction / 7.1: hydroboration / 7.2: Suzuki coupling / 8.1: Hydrolysis / 9.1: Cyclization / 10.1: Oxidation;
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

: 197233-32-2
(Z)-(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]-6-triphenylsilanyloxy-oxacyclohexadec-13-ene-2,4-dione

Guidance literature:: Multi-step reaction with 11 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

11.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

With 2,6-dimethylpyridine; oxalyl dichloride; potassium hexamethylsilazane; Dess-Martin periodane; 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 / 11.1: Oxidation;
DOI:10.1021/ja971946k