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

Base Information

Chemical Name:Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-13-oxo-11-triphenylsilanyloxy-tridec-3-enyl ester
CAS No.:186692-70-6
Molecular Formula:C₅₀H₆₉NO₅SSi₂
Molecular Weight:852.339
Hs Code.:

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

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

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

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

There total 36 articles about Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-13-oxo-11-triphenylsilanyloxy-tridec-3-enyl ester 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: 85.0%

: 186692-69-3
Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-(tert-butyl-dimethyl-silanyloxy)-13,13-dimethoxy-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-11-triphenylsilanyloxy-tridec-3-enyl ester

: 186692-70-6
Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-13-oxo-11-triphenylsilanyloxy-tridec-3-enyl ester

Guidance literature:: With toluene-4-sulfonic acid; In 1,4-dioxane; water; at 55 ℃; for 3h;
DOI:10.1021/ja971946k

Reference yield:

: 186692-77-3
[(S)-4-Methoxymethoxy-5-(tetrahydro-pyran-2-yloxy)-pent-1-ynyl]-trimethyl-silane

: 186692-70-6
Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-13-oxo-11-triphenylsilanyloxy-tridec-3-enyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 95 percent / pyridinium p-toluenesulfonate / methanol / 20 °C

2.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

2.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: diethyl ether / 0 - 20 °C

4.1: 93 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetra-n-propylammonium perruthenate / CH₂Cl₂ / 0 - 20 °C

5.1: n-BuLi / tetrahydrofuran / -78 °C

5.2: 97 percent / tetrahydrofuran / -78 - 20 °C

6.1: 64 percent / N-iodosuccinimide; AgNO₃ / acetone

7.1: 65 percent / dicyclohexylborane; AcOH / diethyl ether

8.1: 86 percent / PhSH; BF₃*OEt₂ / CH₂Cl₂ / 20 °C

9.1: 99 percent / pyridine; 4-DMAP / CH₂Cl₂ / 20 °C

10.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C

10.2: 75 percent / Cs₂CO₃; Ph₃As; H₂O / PdCl₂(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C

11.1: 85 percent / pTSA*H₂O / dioxane; H₂O / 3 h / 55 °C

With pyridine; dmap; N-iodo-succinimide; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; silver nitrate; acetic acid; dimethyl sulfoxide; thiophenol; 4-methylmorpholine N-oxide; 9-bora-bicyclo[3.3.1]nonane; tetrapropylammonium perruthennate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; acetone; 1.1: methanolysis / 2.1: Condensation / 2.2: Elimination / 3.1: Grignard reaction / 4.1: Oxidation / 5.1: Metallation / 5.2: Emmons reaction / 6.1: iododesilylation / 7.1: Reduction / 8.1: dealkylation / 9.1: Acetylation / 10.1: hydroboration / 10.2: Suzuki coupling / 11.1: Hydrolysis;
DOI:10.1021/ja971946k

Reference yield:

: 186692-64-8
(S)-2-Methoxymethoxy-5-trimethylsilanyl-pent-4-yn-1-ol

: 186692-70-6
Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-13-oxo-11-triphenylsilanyloxy-tridec-3-enyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

1.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: diethyl ether / 0 - 20 °C

3.1: 93 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetra-n-propylammonium perruthenate / CH₂Cl₂ / 0 - 20 °C

4.1: n-BuLi / tetrahydrofuran / -78 °C

4.2: 97 percent / tetrahydrofuran / -78 - 20 °C

5.1: 64 percent / N-iodosuccinimide; AgNO₃ / acetone

6.1: 65 percent / dicyclohexylborane; AcOH / diethyl ether

7.1: 86 percent / PhSH; BF₃*OEt₂ / CH₂Cl₂ / 20 °C

8.1: 99 percent / pyridine; 4-DMAP / CH₂Cl₂ / 20 °C

9.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C

9.2: 75 percent / Cs₂CO₃; Ph₃As; H₂O / PdCl₂(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C

10.1: 85 percent / pTSA*H₂O / dioxane; H₂O / 3 h / 55 °C

With pyridine; dmap; N-iodo-succinimide; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; toluene-4-sulfonic acid; silver nitrate; acetic acid; dimethyl sulfoxide; thiophenol; 4-methylmorpholine N-oxide; 9-bora-bicyclo[3.3.1]nonane; tetrapropylammonium perruthennate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; acetone; 1.1: Condensation / 1.2: Elimination / 2.1: Grignard reaction / 3.1: Oxidation / 4.1: Metallation / 4.2: Emmons reaction / 5.1: iododesilylation / 6.1: Reduction / 7.1: dealkylation / 8.1: Acetylation / 9.1: hydroboration / 9.2: Suzuki coupling / 10.1: Hydrolysis;
DOI:10.1021/ja971946k