(S)-4-benzyl-3-((1E,3Z)-1-((tert-butyldimethylsilyl)oxy)-2-methylpenta-1,3-dien-1-yl)oxazolidin-2-one

Base Information

Chemical Name:(S)-4-benzyl-3-((1E,3Z)-1-((tert-butyldimethylsilyl)oxy)-2-methylpenta-1,3-dien-1-yl)oxazolidin-2-one
CAS No.:1364680-56-7
Molecular Formula:C₂₂H₃₃NO₃Si
Molecular Weight:387.594
Hs Code.:

Synonyms:(S)-4-benzyl-3-((1E,3Z)-1-((tert-butyldimethylsilyl)oxy)-2-methylpenta-1,3-dien-1-yl)oxazolidin-2-one

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Chemical Property of (S)-4-benzyl-3-((1E,3Z)-1-((tert-butyldimethylsilyl)oxy)-2-methylpenta-1,3-dien-1-yl)oxazolidin-2-one

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Technology Process of (S)-4-benzyl-3-((1E,3Z)-1-((tert-butyldimethylsilyl)oxy)-2-methylpenta-1,3-dien-1-yl)oxazolidin-2-one

There total 3 articles about (S)-4-benzyl-3-((1E,3Z)-1-((tert-butyldimethylsilyl)oxy)-2-methylpenta-1,3-dien-1-yl)oxazolidin-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: 92.0%

: 1364680-50-1
(4S)-4-benzyl-3-((Z)-2-methylpent-3-enoyl)oxazolidin-2-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1364680-56-7
(S)-4-benzyl-3-((1E,3Z)-1-((tert-butyldimethylsilyl)oxy)-2-methylpenta-1,3-dien-1-yl)oxazolidin-2-one

Guidance literature:: (4S)-4-benzyl-3-((Z)-2-methylpent-3-enoyl)oxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1.5h; Inert atmosphere;

tert-butyldimethylsilyl chloride; In tetrahydrofuran; at -78 ℃; for 1.25h; Inert atmosphere;
DOI:10.1021/ol300353w

Reference yield:

: 2258-55-1,33603-30-4,33599-69-8
2-Methyl-cis-3-pentensaeuremethylester

: 1364680-56-7
(S)-4-benzyl-3-((1E,3Z)-1-((tert-butyldimethylsilyl)oxy)-2-methylpenta-1,3-dien-1-yl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: water; lithium hydroxide / methanol; diethyl ether / 5 h / 20 °C

2.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 16 h / 0 - 20 °C

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere

3.2: 1.25 h / -78 °C / Inert atmosphere

With dmap; water; sodium hexamethyldisilazane; dicyclohexyl-carbodiimide; lithium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/ol300353w

Reference yield:

: 15790-87-1,818-59-7,15790-88-2
Methyl (E)-2-pentenoate

: 1364680-56-7
(S)-4-benzyl-3-((1E,3Z)-1-((tert-butyldimethylsilyl)oxy)-2-methylpenta-1,3-dien-1-yl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: 0.33 h / -78 °C / Inert atmosphere

2.1: water; lithium hydroxide / methanol; diethyl ether / 5 h / 20 °C

3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 16 h / 0 - 20 °C

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere

4.2: 1.25 h / -78 °C / Inert atmosphere

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; water; sodium hexamethyldisilazane; dicyclohexyl-carbodiimide; lithium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ol300353w