diethyl (S)-(Z)-1-tert-butyldimethylsilyloxy-6-phenyl-2-hexen-4-yl phosphate

Base Information

Chemical Name:diethyl (S)-(Z)-1-tert-butyldimethylsilyloxy-6-phenyl-2-hexen-4-yl phosphate
CAS No.:1378962-68-5
Molecular Formula:C₂₂H₃₉O₅PSi
Molecular Weight:442.608
Hs Code.:

Synonyms:diethyl (S)-(Z)-1-tert-butyldimethylsilyloxy-6-phenyl-2-hexen-4-yl phosphate

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Chemical Property of diethyl (S)-(Z)-1-tert-butyldimethylsilyloxy-6-phenyl-2-hexen-4-yl phosphate

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Technology Process of diethyl (S)-(Z)-1-tert-butyldimethylsilyloxy-6-phenyl-2-hexen-4-yl phosphate

There total 9 articles about diethyl (S)-(Z)-1-tert-butyldimethylsilyloxy-6-phenyl-2-hexen-4-yl phosphate 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: 61.0%

: 1016652-27-9
(S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-ol

: 814-49-3
diethyl chlorophosphate

: 1378962-68-5
diethyl (S)-(Z)-1-tert-butyldimethylsilyloxy-6-phenyl-2-hexen-4-yl phosphate

Guidance literature:: With pyridine; dmap; at 20 ℃; for 3h; optical yield given as %ee; Inert atmosphere;
DOI:10.1002/anie.201200809

Reference yield:

: 329313-35-1
C₁₁H₁₃ClO

: 1378962-68-5
diethyl (S)-(Z)-1-tert-butyldimethylsilyloxy-6-phenyl-2-hexen-4-yl phosphate

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 12 h / 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

3.2: 5 h / -78 - 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

5.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / -50 °C / Inert atmosphere

6.1: quinoline; Pd-BaSO₄; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr / Inert atmosphere

7.1: pyridine; dmap / 3 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; quinoline; dmap; n-butyllithium; Pd-BaSO₄; tetrabutyl ammonium fluoride; hydrogen; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.201200809

Reference yield:

: 1016652-45-1
C₁₈H₂₈O₂Si

: 1378962-68-5
diethyl (S)-(Z)-1-tert-butyldimethylsilyloxy-6-phenyl-2-hexen-4-yl phosphate

Guidance literature:: Multi-step reaction with 4 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

2: 1H-imidazole / N,N-dimethyl-formamide / 2 h / -50 °C / Inert atmosphere

3: quinoline; Pd-BaSO₄; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr / Inert atmosphere

4: pyridine; dmap / 3 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; quinoline; dmap; Pd-BaSO₄; tetrabutyl ammonium fluoride; hydrogen; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1002/anie.201200809