(5Z,8Z)-9-{(4S,5S)-5-[(Z)-(R)-1-(tert-Butyl-diphenyl-silanyloxy)-non-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-nona-5,8-dienoic acid methyl ester

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Chemical Name:(5Z,8Z)-9-{(4S,5S)-5-[(Z)-(R)-1-(tert-Butyl-diphenyl-silanyloxy)-non-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-nona-5,8-dienoic acid methyl ester
CAS No.:139723-71-0
Molecular Formula:C₄₀H₅₈O₅Si
Molecular Weight:646.983
Hs Code.:

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Chemical Property of (5Z,8Z)-9-{(4S,5S)-5-[(Z)-(R)-1-(tert-Butyl-diphenyl-silanyloxy)-non-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-nona-5,8-dienoic acid methyl ester

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Technology Process of (5Z,8Z)-9-{(4S,5S)-5-[(Z)-(R)-1-(tert-Butyl-diphenyl-silanyloxy)-non-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-nona-5,8-dienoic acid methyl ester

There total 14 articles about (5Z,8Z)-9-{(4S,5S)-5-[(Z)-(R)-1-(tert-Butyl-diphenyl-silanyloxy)-non-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-nona-5,8-dienoic acid methyl 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:

: 139723-70-9
9-{(4S,5S)-5-[(Z)-(R)-1-(tert-Butyl-diphenyl-silanyloxy)-non-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-nona-5,8-diynoic acid methyl ester

: 139723-71-0
(5Z,8Z)-9-{(4S,5S)-5-[(Z)-(R)-1-(tert-Butyl-diphenyl-silanyloxy)-non-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-nona-5,8-dienoic acid methyl ester

Guidance literature:: With hydrogen; Lindlar's catalyst; In ethanol;
DOI:10.1016/S0040-4039(00)77695-7

Reference yield:

: 1720-37-2
2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran

: 139723-71-0
(5Z,8Z)-9-{(4S,5S)-5-[(Z)-(R)-1-(tert-Butyl-diphenyl-silanyloxy)-non-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-nona-5,8-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1) n-BuLi, 2) TsCl, py, LiBr

2: 1) Jones' reagent / 2) ether

3: 1) n-BuLi, CuI / 1) THF, HMPA, -78 deg C to 0 deg C, 30 min, 2) THF, -78 deg C to rt, 2 h

4: H₂ / Pd-CaCO₃ / ethanol

With pyridine; copper(l) iodide; n-butyllithium; jones' reagent; hydrogen; p-toluenesulfonyl chloride; lithium bromide; Lindlar's catalyst; In ethanol;
DOI:10.1016/S0040-4039(00)77695-7

Reference yield:

: 4762-26-9
hexyltriphenylphosphonium bromide

: 139723-71-0
(5Z,8Z)-9-{(4S,5S)-5-[(Z)-(R)-1-(tert-Butyl-diphenyl-silanyloxy)-non-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-nona-5,8-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 70 percent / NaNH₂ / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -78 deg C -> rt

2: aq. AcOH / 6 h / 28 °C

3: NaIO₄ / acetonitrile; H₂O / 3 h

4: NaBH₄ / ethanol / 0.5 h

5: 90 percent / PPh₃, CCl₄ / 6 h / Heating

6: 86 percent / LiNH₂, liq. NH₃ / 0.5 h / -33 °C

7: 94 percent / imidazole / dimethylformamide / 8 h / 60 °C

8: 1) n-BuLi, CuI / 1) THF, HMPA, -78 deg C to 0 deg C, 30 min, 2) THF, -78 deg C to rt, 2 h

9: H₂ / Pd-CaCO₃ / ethanol

With 1H-imidazole; tetrachloromethane; sodium tetrahydroborate; sodium periodate; copper(l) iodide; n-butyllithium; lithium amide; ammonia; hydrogen; sodium amide; acetic acid; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(00)77695-7