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

Base Information

Chemical Name:(5S,6S)-((2S,3R)-2-methyl-1-(tosyloxy)hex-5-en-3-yl) 5-(tert-butyldimethylsilyloxy)-6-methylnon-8-enoate
CAS No.:1361550-95-9
Molecular Formula:C₃₀H₅₀O₆SSi
Molecular Weight:566.875
Hs Code.:

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

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Chemical Property of (5S,6S)-((2S,3R)-2-methyl-1-(tosyloxy)hex-5-en-3-yl) 5-(tert-butyldimethylsilyloxy)-6-methylnon-8-enoate

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Technology Process of (5S,6S)-((2S,3R)-2-methyl-1-(tosyloxy)hex-5-en-3-yl) 5-(tert-butyldimethylsilyloxy)-6-methylnon-8-enoate

There total 5 articles about (5S,6S)-((2S,3R)-2-methyl-1-(tosyloxy)hex-5-en-3-yl) 5-(tert-butyldimethylsilyloxy)-6-methylnon-8-enoate 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:

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

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

Guidance literature:: Multi-step reaction with 4 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

With 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:

: 84341-89-9
(2S)-(+)-2-methyl-3-(toluene-4-sulfonyloxy)propionic acid methyl ester

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

Guidance literature:: Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / toluene / -78 - 20 °C / Inert atmosphere

1.2: 5 h / Inert atmosphere

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 10 - 20 °C / Inert atmosphere

3.1: diethyl ether / -78 °C / Inert atmosphere

3.2: 12 h / -78 - 20 °C / Inert atmosphere

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

With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; In diethyl ether; dichloromethane; toluene;
DOI:10.1002/chem.201102542

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

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

Guidance literature:: Multi-step reaction with 6 steps

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

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

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

4: sodium iodide / acetone / 14 h / Inert atmosphere; Reflux; Darkness

5: iron(III) chloride; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 1 h / 0 °C

6: dicyclohexyl-carbodiimide; dmap / dichloromethane / 14.5 h / 0 - 20 °C / Inert atmosphere

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; ethyl acetate; acetone;