(2S)-2-((2R,7S,8S,E)-8-(tert-butyldimethylsilyloxy)-7-methyl-12-oxo-1-oxacyclododec-4-en-2-yl)propyl-4-methylbenzene-1-sulfonate

Base Information

Chemical Name:(2S)-2-((2R,7S,8S,E)-8-(tert-butyldimethylsilyloxy)-7-methyl-12-oxo-1-oxacyclododec-4-en-2-yl)propyl-4-methylbenzene-1-sulfonate
CAS No.:1361551-05-4
Molecular Formula:C₂₈H₄₆O₆SSi
Molecular Weight:538.821
Hs Code.:

Synonyms:(2S)-2-((2R,7S,8S,E)-8-(tert-butyldimethylsilyloxy)-7-methyl-12-oxo-1-oxacyclododec-4-en-2-yl)propyl-4-methylbenzene-1-sulfonate

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Chemical Property of (2S)-2-((2R,7S,8S,E)-8-(tert-butyldimethylsilyloxy)-7-methyl-12-oxo-1-oxacyclododec-4-en-2-yl)propyl-4-methylbenzene-1-sulfonate

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Technology Process of (2S)-2-((2R,7S,8S,E)-8-(tert-butyldimethylsilyloxy)-7-methyl-12-oxo-1-oxacyclododec-4-en-2-yl)propyl-4-methylbenzene-1-sulfonate

There total 7 articles about (2S)-2-((2R,7S,8S,E)-8-(tert-butyldimethylsilyloxy)-7-methyl-12-oxo-1-oxacyclododec-4-en-2-yl)propyl-4-methylbenzene-1-sulfonate 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: 83.0%

: 1361550-95-9
(5S,6S)-((2S,3R)-2-methyl-1-(tosyloxy)hex-5-en-3-yl) 5-(tert-butyldimethylsilyloxy)-6-methylnon-8-enoate

: 1361551-05-4
(2S)-2-((2R,7S,8S,E)-8-(tert-butyldimethylsilyloxy)-7-methyl-12-oxo-1-oxacyclododec-4-en-2-yl)propyl-4-methylbenzene-1-sulfonate

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 90 ℃; for 0.166667h; stereoselective reaction; Inert atmosphere; Microwave irradiation;
DOI:10.1002/chem.201102542

Reference yield:

: 501015-40-3
(2S,3S)-(+)-toluene-4-sulfonic acid 3-hydroxy-2-methylhex-5-enyl ester

: 1361551-05-4
(2S)-2-((2R,7S,8S,E)-8-(tert-butyldimethylsilyloxy)-7-methyl-12-oxo-1-oxacyclododec-4-en-2-yl)propyl-4-methylbenzene-1-sulfonate

Guidance literature:: Multi-step reaction with 7 steps

1: 1H-imidazole / dichloromethane / 72 h / 20 °C

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 0.33 h / 90 °C / Microwave irradiation; Inert atmosphere

3: hydrogen; palladium(II) hydroxide / 20 °C / Inert atmosphere

4: sodium iodide / acetone / 18 h / 65 °C / Inert atmosphere; Reflux; Darkness

5: iron(III) chloride; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 0 °C / Inert atmosphere

6: dmap; dicyclohexyl-carbodiimide / dichloromethane / 7.5 h / 0 - 20 °C / Inert atmosphere

7: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 0.17 h / 90 °C / Inert atmosphere; Microwave irradiation

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; iron(III) chloride; N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium(II) hydroxide; dicyclohexyl-carbodiimide; sodium iodide; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1002/chem.201102542

Reference yield:

: (5S,6S)-5-(tert-butyldimethylsilyloxy)-6-methyl-7-(tosyloxy)heptanoic acid

: 1361551-05-4
(2S)-2-((2R,7S,8S,E)-8-(tert-butyldimethylsilyloxy)-7-methyl-12-oxo-1-oxacyclododec-4-en-2-yl)propyl-4-methylbenzene-1-sulfonate

Guidance literature:: Multi-step reaction with 5 steps

1: hydrogen; palladium(II) hydroxide / 20 °C / Inert atmosphere

2: sodium iodide / acetone / 18 h / 65 °C / Inert atmosphere; Reflux; Darkness

3: iron(III) chloride; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 0 °C / Inert atmosphere

4: dmap; dicyclohexyl-carbodiimide / dichloromethane / 7.5 h / 0 - 20 °C / Inert atmosphere

5: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 0.17 h / 90 °C / Inert atmosphere; Microwave irradiation

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; iron(III) chloride; N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium(II) hydroxide; dicyclohexyl-carbodiimide; sodium iodide; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1002/chem.201102542