(2S,3R,Z)-2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-3-fluorohex-4-en-1-ol

Base Information

Chemical Name:(2S,3R,Z)-2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-3-fluorohex-4-en-1-ol
CAS No.:1316643-92-1
Molecular Formula:C₂₈H₄₃FO₃Si₂
Molecular Weight:502.817
Hs Code.:

Synonyms:(2S,3R,Z)-2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-3-fluorohex-4-en-1-ol

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Chemical Property of (2S,3R,Z)-2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-3-fluorohex-4-en-1-ol

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Technology Process of (2S,3R,Z)-2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-3-fluorohex-4-en-1-ol

There total 8 articles about (2S,3R,Z)-2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-3-fluorohex-4-en-1-ol 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: 83.0%

: 1316643-91-0
(8R,9S,Z)-9-(benzyloxymethyl)-8-fluoro-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene

: 1316643-92-1
(2S,3R,Z)-2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-3-fluorohex-4-en-1-ol

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,2-dichloro-ethane; at 50 ℃; for 8h;
DOI:10.1021/jo200611w

Reference yield:

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

: 1316643-92-1
(2S,3R,Z)-2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-3-fluorohex-4-en-1-ol

Guidance literature:: Multi-step reaction with 8 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

With 1H-imidazole; 2,6-dimethylpyridine; quinoline; titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; Pd-BaSO₄; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydride; triethylamine tris(hydrogen fluoride); 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane; acetone; 1.1: Sharpless epoxidation / 1.2: Sharpless epoxidation;
DOI:10.1021/jo200611w

Reference yield:

: 1316643-86-3
(Z,4R,5S)-6-(benzyloxy)-4-fluorohex-2-ene-1,5-diol

: 1316643-92-1
(2S,3R,Z)-2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-3-fluorohex-4-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

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

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

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

With 1H-imidazole; 2,6-dimethylpyridine; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/jo200611w