(E)-4(R)-<(tert-butyldiphenylsilyl)oxy>-6(S)-<2-<2,6-dimethyl-4-(4-fluorophenyl)pyridin-3-yl>ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

Base Information

Chemical Name:(E)-4(R)-<(tert-butyldiphenylsilyl)oxy>-6(S)-<2-<2,6-dimethyl-4-(4-fluorophenyl)pyridin-3-yl>ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one
CAS No.:122254-03-9
Molecular Formula:C₃₆H₃₈FNO₃Si
Molecular Weight:579.787
Hs Code.:

Synonyms:(E)-4(R)-<(tert-butyldiphenylsilyl)oxy>-6(S)-<2-<2,6-dimethyl-4-(4-fluorophenyl)pyridin-3-yl>ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

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Chemical Property of (E)-4(R)-<(tert-butyldiphenylsilyl)oxy>-6(S)-<2-<2,6-dimethyl-4-(4-fluorophenyl)pyridin-3-yl>ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

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Technology Process of (E)-4(R)-<(tert-butyldiphenylsilyl)oxy>-6(S)-<2-<2,6-dimethyl-4-(4-fluorophenyl)pyridin-3-yl>ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

There total 8 articles about (E)-4(R)-<(tert-butyldiphenylsilyl)oxy>-6(S)-<2-<2,6-dimethyl-4-(4-fluorophenyl)pyridin-3-yl>ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one 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: 76.0%

: 122253-84-3
(E)-4(R)-<(tert-butyldiphenylsilyl)oxy>-6(S)-<2-<2,6-dimethyl-4-(4-fluorophenyl)pyridin-3-yl>ethenyl>-2-hydroxy-3,4,5,6-tetrahydro-2H-pyran

: 122254-03-9
(E)-4(R)-<(tert-butyldiphenylsilyl)oxy>-6(S)-<2-<2,6-dimethyl-4-(4-fluorophenyl)pyridin-3-yl>ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

Guidance literature:: With N-iodo-succinimide; tetra-(n-butyl)ammonium iodide; In dichloromethane; for 2h; Ambient temperature;
DOI:10.1021/jm00163a010

Reference yield:

: 65300-29-0,1611-38-7
4-(4-fluorophenyl)but-3-en-2-one

: 122254-03-9
(E)-4(R)-<(tert-butyldiphenylsilyl)oxy>-6(S)-<2-<2,6-dimethyl-4-(4-fluorophenyl)pyridin-3-yl>ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 72 percent / KOH, EtOH / diethyl ether / 3 h

2: 91 percent / ammonium acetate, FCl₃*6H₂O / acetic acid / 4 h / Heating

3: 93 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

4: 79 percent / PBr₃ / toluene; CH₂Cl₂ / 1 h / Ambient temperature

5: 89 percent / toluene / 5 h / Heating

6: 1.) 1.6 M n-BuLi / 1.) THF, hexane, 0.5 h, 2.) 1 h

7: 63 percent / aq. HOAc / tetrahydrofuran / 48 h / Heating

8: 76 percent / N-iodosuccinimide, tetra-n-butylammonium iodide / CH₂Cl₂ / 2 h / Ambient temperature

With ammonium acetate; potassium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; n-butyllithium; ethanol; phosphorus tribromide; tetra-(n-butyl)ammonium iodide; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; toluene;
DOI:10.1021/jm00163a010

Reference yield:

: 122253-19-4
bromo<2,6-dimethyl-4-(4-fluorophenyl)pyridin-3-yl>methane

: 122254-03-9
(E)-4(R)-<(tert-butyldiphenylsilyl)oxy>-6(S)-<2-<2,6-dimethyl-4-(4-fluorophenyl)pyridin-3-yl>ethenyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / toluene / 5 h / Heating

2: 1.) 1.6 M n-BuLi / 1.) THF, hexane, 0.5 h, 2.) 1 h

3: 63 percent / aq. HOAc / tetrahydrofuran / 48 h / Heating

4: 76 percent / N-iodosuccinimide, tetra-n-butylammonium iodide / CH₂Cl₂ / 2 h / Ambient temperature

With N-iodo-succinimide; n-butyllithium; tetra-(n-butyl)ammonium iodide; acetic acid; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jm00163a010