(5E,7E,10Z)-3β-(tert-butyldimethylsilyloxy)-19-fluoro-9,10-seco-5,7,10(19)-cholestatriene

Base Information

Chemical Name:(5E,7E,10Z)-3β-(tert-butyldimethylsilyloxy)-19-fluoro-9,10-seco-5,7,10(19)-cholestatriene
CAS No.:182232-27-5
Molecular Formula:C₃₃H₅₇FOSi
Molecular Weight:516.899
Hs Code.:

Synonyms:(5E,7E,10Z)-3β-(tert-butyldimethylsilyloxy)-19-fluoro-9,10-seco-5,7,10(19)-cholestatriene

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Chemical Property of (5E,7E,10Z)-3β-(tert-butyldimethylsilyloxy)-19-fluoro-9,10-seco-5,7,10(19)-cholestatriene

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Technology Process of (5E,7E,10Z)-3β-(tert-butyldimethylsilyloxy)-19-fluoro-9,10-seco-5,7,10(19)-cholestatriene

There total 6 articles about (5E,7E,10Z)-3β-(tert-butyldimethylsilyloxy)-19-fluoro-9,10-seco-5,7,10(19)-cholestatriene 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: 65.5%

: 182232-22-0
tert-Butyl-{(1S,3R,5S)-3-[(1R,3aS,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-1-fluoro-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-yloxy}-dimethyl-silane

: 182232-32-2
(5Z,7E,10E)-3β-(tert-butyldimethylsilyloxy)-19-fluoro-9,10-seco-5,7,10(19)-cholestatriene

: 182232-27-5
(5E,7E,10Z)-3β-(tert-butyldimethylsilyloxy)-19-fluoro-9,10-seco-5,7,10(19)-cholestatriene

Guidance literature:: With sodium hydrogencarbonate; In ethanol; at 80 ℃; for 1.5h;
DOI:10.1248/cpb.48.1484

Reference yield: 59.7%

: 182232-13-9
tert-Butyl-{(1R,3S,5S)-3-[(1R,3aS,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-1-fluoro-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-yloxy}-dimethyl-silane

: 182232-32-2
(5Z,7E,10E)-3β-(tert-butyldimethylsilyloxy)-19-fluoro-9,10-seco-5,7,10(19)-cholestatriene

: 182232-27-5
(5E,7E,10Z)-3β-(tert-butyldimethylsilyloxy)-19-fluoro-9,10-seco-5,7,10(19)-cholestatriene

Guidance literature:: With sodium hydrogencarbonate; In ethanol; at 80 ℃; for 1.5h;
DOI:10.1248/cpb.48.1484

Reference yield:

: 182232-03-7
tert-Butyl-{(3R,5S)-3-[(1R,3aS,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-yloxy}-dimethyl-silane

: 182232-27-5
(5E,7E,10Z)-3β-(tert-butyldimethylsilyloxy)-19-fluoro-9,10-seco-5,7,10(19)-cholestatriene

Guidance literature:: Multi-step reaction with 2 steps

1: 27.4 percent / HMPA; (PhSO₂)2NF; LiHMDS / tetrahydrofuran / 0.17 h / -78 °C

2: 65.5 percent / NaHCO₃ / ethanol / 1.5 h / 80 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydrogencarbonate; N-fluorobis(benzenesulfon)imide; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol;
DOI:10.1248/cpb.48.1484