(8R,9S,Z)-8-fluoro-9-(4-fluorostyryl)-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene

Base Information

Chemical Name:(8R,9S,Z)-8-fluoro-9-(4-fluorostyryl)-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene
CAS No.:1316643-99-8
Molecular Formula:C₃₅H₄₆F₂O₂Si₂
Molecular Weight:592.917
Hs Code.:

Synonyms:(8R,9S,Z)-8-fluoro-9-(4-fluorostyryl)-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene

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Chemical Property of (8R,9S,Z)-8-fluoro-9-(4-fluorostyryl)-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene

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Technology Process of (8R,9S,Z)-8-fluoro-9-(4-fluorostyryl)-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene

There total 11 articles about (8R,9S,Z)-8-fluoro-9-(4-fluorostyryl)-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene 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: 52.0%

: 1316643-93-2
(2S,3R,Z)-2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-3-fluorohex-4-enal

: 63909-58-0
diethyl (4-fluorobenzyl)phosphonate

: 1316643-99-8
(8R,9S,Z)-8-fluoro-9-(4-fluorostyryl)-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene

Guidance literature:: diethyl (4-fluorobenzyl)phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -30 ℃; for 0.833333h; Inert atmosphere;

(2S,3R,Z)-2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-3-fluorohex-4-enal; In tetrahydrofuran; hexane; at 20 ℃; for 3h; optical yield given as %de; stereoselective reaction; Inert atmosphere;
DOI:10.1021/jo200611w

Reference yield:

: 1316643-85-2
(4R,5S)-6-(benzyloxy)-4-fluorohex-2-yne-1,5-diol

: 1316643-99-8
(8R,9S,Z)-8-fluoro-9-(4-fluorostyryl)-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene

Guidance literature:: Multi-step reaction with 6 steps

1.1: quinoline; Pd-BaSO₄; hydrogen / hexane; acetone / 1 h / 20 °C

2.1: 1H-imidazole / dichloromethane / 0.5 h / 20 °C

3.1: 2,6-dimethylpyridine / dichloromethane / 12 h / -40 - 20 °C

4.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,2-dichloro-ethane / 8 h / 50 °C

5.1: sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 0.58 h / -30 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.83 h / -78 - -30 °C / Inert atmosphere

6.2: 3 h / 20 °C / Inert atmosphere

With 1H-imidazole; 2,6-dimethylpyridine; quinoline; n-butyllithium; Pd-BaSO₄; water; hydrogen; sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; acetone; 6.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jo200611w

Reference yield:

: 1175994-84-9
(E)-6-(tert-butyldimethylsilyloxy)hex-2-en-4-yn-1-ol

: 1316643-99-8
(8R,9S,Z)-8-fluoro-9-(4-fluorostyryl)-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene

Guidance literature:: Multi-step reaction with 10 steps

1.1: titanium(IV) isopropylate; diethyl (2R,3R)-tartrate / dichloromethane / 0.75 h / -20 °C / Molecular sieve

1.2: 18 h / 20 °C / Molecular sieve

2.1: sodium hydride / tetrahydrofuran / 0.33 h / -40 °C / Inert atmosphere

2.2: 2 h / 25 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / -5 °C

4.1: triethylamine tris(hydrogen fluoride) / 70 °C / Inert atmosphere

5.1: quinoline; Pd-BaSO₄; hydrogen / hexane; acetone / 1 h / 20 °C

6.1: 1H-imidazole / dichloromethane / 0.5 h / 20 °C

7.1: 2,6-dimethylpyridine / dichloromethane / 12 h / -40 - 20 °C

8.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,2-dichloro-ethane / 8 h / 50 °C

9.1: sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 0.58 h / -30 °C

10.1: n-butyllithium / tetrahydrofuran; hexane / 0.83 h / -78 - -30 °C / Inert atmosphere

10.2: 3 h / 20 °C / Inert atmosphere

With 1H-imidazole; 2,6-dimethylpyridine; quinoline; titanium(IV) isopropylate; n-butyllithium; diethyl (2R,3R)-tartrate; Pd-BaSO₄; tetrabutyl ammonium fluoride; water; hydrogen; sulfur trioxide pyridine complex; sodium hydride; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; acetone; 1.1: Sharpless epoxidation / 1.2: Sharpless epoxidation / 10.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jo200611w