(5Z,9E)-(R)-10-[(1S,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-pentyl-cyclopentyl]-8-hydroxy-deca-5,9-dienoic acid ethyl ester

Base Information

Chemical Name:(5Z,9E)-(R)-10-[(1S,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-pentyl-cyclopentyl]-8-hydroxy-deca-5,9-dienoic acid ethyl ester
CAS No.:331825-46-8
Molecular Formula:C₄₄H₇₀O₅Si₂
Molecular Weight:735.208
Hs Code.:

(5Z,9E)-(R)-10-[(1S,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-pentyl-cyclopentyl]-8-hydroxy-deca-5,9-dienoic acid ethyl ester

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Chemical Property of (5Z,9E)-(R)-10-[(1S,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-pentyl-cyclopentyl]-8-hydroxy-deca-5,9-dienoic acid ethyl ester

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Technology Process of (5Z,9E)-(R)-10-[(1S,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-pentyl-cyclopentyl]-8-hydroxy-deca-5,9-dienoic acid ethyl ester

There total 2 articles about (5Z,9E)-(R)-10-[(1S,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-pentyl-cyclopentyl]-8-hydroxy-deca-5,9-dienoic acid ethyl 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:

: (5Z,9E)-10-[(1S,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-pentyl-cyclopentyl]-8-oxo-deca-5,9-dienoic acid ethyl ester

: 331825-46-8
(5Z,9E)-(R)-10-[(1S,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-pentyl-cyclopentyl]-8-hydroxy-deca-5,9-dienoic acid ethyl ester

: 331825-43-5
(5Z,9E)-(S)-10-[(1S,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-pentyl-cyclopentyl]-8-hydroxy-deca-5,9-dienoic acid ethyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;
DOI:10.1021/jo001731k

Reference yield:

: 331825-43-5
(5Z,9E)-(S)-10-[(1S,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-pentyl-cyclopentyl]-8-hydroxy-deca-5,9-dienoic acid ethyl ester

: 331825-46-8
(5Z,9E)-(R)-10-[(1S,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-pentyl-cyclopentyl]-8-hydroxy-deca-5,9-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

2: 80 mg / NaBH₄ / methanol / 0.5 h / 0 °C

With sodium tetrahydroborate; Dess-Martin periodane; In methanol; dichloromethane;
DOI:10.1021/jo001731k

Reference yield:

: 331825-46-8
(5Z,9E)-(R)-10-[(1S,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-pentyl-cyclopentyl]-8-hydroxy-deca-5,9-dienoic acid ethyl ester

: 8-epi-F_2t-isoprostane

Guidance literature:: Multi-step reaction with 2 steps

1: 87 percent / TBAF / tetrahydrofuran / 40 h / 20 °C

2: 97 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 2 h / 20 °C

With lithium hydroxide; tetrabutyl ammonium fluoride; In tetrahydrofuran; water;
DOI:10.1021/jo001731k