tert-butyl {(R)-1-[(2R,4R)-4-(dimethylphenylsilyl)-6-oxo-3,4,5,6-tetrahydro-2H-pyran-2-yl]pent-4-en-2-yl}carbonate

Base Information

Chemical Name:tert-butyl {(R)-1-[(2R,4R)-4-(dimethylphenylsilyl)-6-oxo-3,4,5,6-tetrahydro-2H-pyran-2-yl]pent-4-en-2-yl}carbonate
CAS No.:1643685-78-2
Molecular Formula:C₂₃H₃₄O₅Si
Molecular Weight:418.605
Hs Code.:

Synonyms:tert-butyl {(R)-1-[(2R,4R)-4-(dimethylphenylsilyl)-6-oxo-3,4,5,6-tetrahydro-2H-pyran-2-yl]pent-4-en-2-yl}carbonate

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Chemical Property of tert-butyl {(R)-1-[(2R,4R)-4-(dimethylphenylsilyl)-6-oxo-3,4,5,6-tetrahydro-2H-pyran-2-yl]pent-4-en-2-yl}carbonate

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Technology Process of tert-butyl {(R)-1-[(2R,4R)-4-(dimethylphenylsilyl)-6-oxo-3,4,5,6-tetrahydro-2H-pyran-2-yl]pent-4-en-2-yl}carbonate

There total 9 articles about tert-butyl {(R)-1-[(2R,4R)-4-(dimethylphenylsilyl)-6-oxo-3,4,5,6-tetrahydro-2H-pyran-2-yl]pent-4-en-2-yl}carbonate 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: 86.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1643685-76-0
(4R,6R)-4-(dimethylphenylsilyl)-6-[(R)-2-hydroxypent-4-en-1-yl]-3,4,5,6-tetrahydro-2H-pyran-2-one

: 1643685-78-2
tert-butyl {(R)-1-[(2R,4R)-4-(dimethylphenylsilyl)-6-oxo-3,4,5,6-tetrahydro-2H-pyran-2-yl]pent-4-en-2-yl}carbonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;
DOI:10.1002/ejoc.201400145

Reference yield:

: 1643685-69-1
(4S,6R)-6-[(ethenesulfonyl)oxy]nona-1,8-dien-4-yl (E)-but-2-enoate

: 1643685-78-2
tert-butyl {(R)-1-[(2R,4R)-4-(dimethylphenylsilyl)-6-oxo-3,4,5,6-tetrahydro-2H-pyran-2-yl]pent-4-en-2-yl}carbonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: Schwartz's reagent / toluene / 3 h / 100 °C / Inert atmosphere

2.1: lithium / tetrahydrofuran / 18 h / -10 °C / Inert atmosphere

2.2: 3 h / -78 - -50 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

4.1: triethylamine; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

With dmap; Schwartz's reagent; tetrabutyl ammonium fluoride; lithium; triethylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/ejoc.201400145

Reference yield:

: 1643685-75-9
(4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-2-one

: 1643685-78-2
tert-butyl {(R)-1-[(2R,4R)-4-(dimethylphenylsilyl)-6-oxo-3,4,5,6-tetrahydro-2H-pyran-2-yl]pent-4-en-2-yl}carbonate

Guidance literature:: Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

2: triethylamine; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.201400145