(4R,5S)-4-allyl-5-[(2S)-3-tert-butyldiphenylsiloxy-2-methylpropyl]dihydrofuran-2(3H)-one

Base Information

Chemical Name:(4R,5S)-4-allyl-5-[(2S)-3-tert-butyldiphenylsiloxy-2-methylpropyl]dihydrofuran-2(3H)-one
CAS No.:1417803-54-3
Molecular Formula:C₂₇H₃₆O₃Si
Molecular Weight:436.667
Hs Code.:

Synonyms:(4R,5S)-4-allyl-5-[(2S)-3-tert-butyldiphenylsiloxy-2-methylpropyl]dihydrofuran-2(3H)-one

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Chemical Property of (4R,5S)-4-allyl-5-[(2S)-3-tert-butyldiphenylsiloxy-2-methylpropyl]dihydrofuran-2(3H)-one

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Technology Process of (4R,5S)-4-allyl-5-[(2S)-3-tert-butyldiphenylsiloxy-2-methylpropyl]dihydrofuran-2(3H)-one

There total 2 articles about (4R,5S)-4-allyl-5-[(2S)-3-tert-butyldiphenylsiloxy-2-methylpropyl]dihydrofuran-2(3H)-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: 39.0%

: 75-77-4
chloro-trimethyl-silane

: 1417803-51-0
(5S)-5-[(2S)-3-(tert-butyldiphenylsiloxy)-2-methylpropyl]furan-2(5H)-one

: 2622-05-1
allylmagnesium bromide

: 1417803-54-3
(4R,5S)-4-allyl-5-[(2S)-3-tert-butyldiphenylsiloxy-2-methylpropyl]dihydrofuran-2(3H)-one

: 1417803-55-4
C₃₀H₄₄O₃Si₂

Guidance literature:: With copper(l) iodide; lithium bromide; In tetrahydrofuran; at -78 - -40 ℃; for 4h; Reagent/catalyst; Temperature; Inert atmosphere;
DOI:10.1016/j.tet.2012.11.077

Reference yield: 21.0%

: 1417803-51-0
(5S)-5-[(2S)-3-(tert-butyldiphenylsiloxy)-2-methylpropyl]furan-2(5H)-one

: 2C₄H₇^(1-)*Cu⁽¹⁺⁾*CN^(1-)*2Li⁽¹⁺⁾

: 1417803-54-3
(4R,5S)-4-allyl-5-[(2S)-3-tert-butyldiphenylsiloxy-2-methylpropyl]dihydrofuran-2(3H)-one

Guidance literature:: In tetrahydrofuran; at -78 - 0 ℃;
DOI:10.1016/j.tet.2012.11.077

Reference yield:

: 1417803-54-3
(4R,5S)-4-allyl-5-[(2S)-3-tert-butyldiphenylsiloxy-2-methylpropyl]dihydrofuran-2(3H)-one

: 26791-73-1,30890-35-8,119478-96-5
(-)-xanthatin

Guidance literature:: Multi-step reaction with 7 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4.08 h / 0 - 20 °C / Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane / 0.33 h / 0 - 20 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / 20 °C

5.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

5.2: 1.33 h / -78 - 0 °C / Inert atmosphere

6.1: lithium diisopropyl amide; N,N,N,N,N,N-hexamethylphosphoric triamide; diphenyl diselenide / hexane; tetrahydrofuran / 2 h / -78 - -40 °C / Inert atmosphere

6.2: 3 h / -40 - 0 °C

7.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 1 h / 45 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; Hoveyda-Grubbs catalyst second generation; diphenyl diselenide; potassium tert-butylate; tetrabutyl ammonium fluoride; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/j.tet.2012.11.077