(2S,3S)-2-{[(tert-butyl)oxycarbonyl]methyl}-3-[4-nitrophenyl]pent-4-enoic acid

Base Information

Chemical Name:(2S,3S)-2-{[(tert-butyl)oxycarbonyl]methyl}-3-[4-nitrophenyl]pent-4-enoic acid
CAS No.:852714-68-2
Molecular Formula:C₁₇H₂₁NO₆
Molecular Weight:335.357
Hs Code.:

Synonyms:(2S,3S)-2-{[(tert-butyl)oxycarbonyl]methyl}-3-[4-nitrophenyl]pent-4-enoic acid

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Chemical Property of (2S,3S)-2-{[(tert-butyl)oxycarbonyl]methyl}-3-[4-nitrophenyl]pent-4-enoic acid

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Technology Process of (2S,3S)-2-{[(tert-butyl)oxycarbonyl]methyl}-3-[4-nitrophenyl]pent-4-enoic acid

There total 7 articles about (2S,3S)-2-{[(tert-butyl)oxycarbonyl]methyl}-3-[4-nitrophenyl]pent-4-enoic acid 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: 95.0%

: 852714-67-1
tert-butyl 3-[((4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)carbonyl]-(3S,4S)-4-[4-nitrophenyl]hex-5-enoate

: 852714-68-2
(2S,3S)-2-{[(tert-butyl)oxycarbonyl]methyl}-3-[4-nitrophenyl]pent-4-enoic acid

Guidance literature:: With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 5h;
DOI:10.1021/jm050059m

Reference yield:

: 852714-66-0
3-[(3R)-3-(4-nitrophenyl)pent-4-enoyl]-(4S)-4-phenyl-1,3-oxazolidin-2-one

: 852714-68-2
(2S,3S)-2-{[(tert-butyl)oxycarbonyl]methyl}-3-[4-nitrophenyl]pent-4-enoic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

1.2: 56 percent / tetrahydrofuran / 1.5 h / -78 - 20 °C

2.1: 95 percent / aq. H₂O₂; LiOH / tetrahydrofuran / 5 h / 20 °C

With lithium hydroxide; dihydrogen peroxide; lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1021/jm050059m

Reference yield:

: 882-06-4
4-nitro-trans-cinnamic acid

: 852714-68-2
(2S,3S)-2-{[(tert-butyl)oxycarbonyl]methyl}-3-[4-nitrophenyl]pent-4-enoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-methylmorpholine / tetrahydrofuran / 0.5 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 26.6 g / tetrahydrofuran; hexane / -78 - 20 °C

3.1: PhSCu / diethyl ether; tetrahydrofuran / -40 °C

3.2: 23 percent / diethyl ether; tetrahydrofuran / 1.1 h / -40 °C

4.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 56 percent / tetrahydrofuran / 1.5 h / -78 - 20 °C

5.1: 95 percent / aq. H₂O₂; LiOH / tetrahydrofuran / 5 h / 20 °C

With 4-methyl-morpholine; lithium hydroxide; n-butyllithium; dihydrogen peroxide; copper(I) thiophenolate; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane;
DOI:10.1021/jm050059m