5-[(2S,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-prop-(Z)-ylidene]-5H-furan-2-one

Base Information

Chemical Name:5-[(2S,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-prop-(Z)-ylidene]-5H-furan-2-one
CAS No.:186806-47-3
Molecular Formula:C₂₅H₄₀O₄Si₂
Molecular Weight:460.761
Hs Code.:

Synonyms:5-[(2S,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-prop-(Z)-ylidene]-5H-furan-2-one

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Chemical Property of 5-[(2S,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-prop-(Z)-ylidene]-5H-furan-2-one

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Technology Process of 5-[(2S,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-prop-(Z)-ylidene]-5H-furan-2-one

There total 4 articles about 5-[(2S,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-prop-(Z)-ylidene]-5H-furan-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: 27.0%

: 1609-92-3
(Z)-3-bromoacrylic acid

: 186806-43-9
(1R,2S)-1,2-bis[(tert-butyldimethylsilyl)oxy]-1-phenylbut-3-yne

: 186806-47-3
5-[(2S,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-prop-(Z)-ylidene]-5H-furan-2-one

: C₄₄H₇₄O₄Si₄

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In acetonitrile; at 22 ℃; for 48h;
DOI:10.1016/S0040-4039(96)01972-7

Reference yield:

: 611-71-2
(R)-Mandelic Acid

: 186806-47-3
5-[(2S,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-prop-(Z)-ylidene]-5H-furan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: p-TsOH / 3 h / Heating

2: imidazole / dimethylformamide / 12 h / 22 °C

3: i-Bu₂AlH / diethyl ether / 0.5 h / -78 °C

4: 55 percent / tetrahydrofuran / 1 h / -78 - 22 °C

5: 96 percent / imidazole / dimethylformamide / 12 h / 22 °C

6: 55 percent / PdCl₂(PPh₃)2, PPh₃, CuI, Et₃N / acetonitrile / 48 h / 22 °C

With 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(96)01972-7

Reference yield:

: 20698-91-3
(R)-methyl mandelate

: 186806-47-3
5-[(2S,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-prop-(Z)-ylidene]-5H-furan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole / dimethylformamide / 12 h / 22 °C

2: i-Bu₂AlH / diethyl ether / 0.5 h / -78 °C

3: 55 percent / tetrahydrofuran / 1 h / -78 - 22 °C

4: 96 percent / imidazole / dimethylformamide / 12 h / 22 °C

5: 55 percent / PdCl₂(PPh₃)2, PPh₃, CuI, Et₃N / acetonitrile / 48 h / 22 °C

With 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(96)01972-7