(2R,3S)-2-(benzyloxycarbonylamino)-3-phenylpent-4-enoic acid

Base Information

Chemical Name:(2R,3S)-2-(benzyloxycarbonylamino)-3-phenylpent-4-enoic acid
CAS No.:953787-40-1
Molecular Formula:C₁₉H₁₉NO₄
Molecular Weight:325.364
Hs Code.:

Synonyms:(2R,3S)-2-(benzyloxycarbonylamino)-3-phenylpent-4-enoic acid

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Chemical Property of (2R,3S)-2-(benzyloxycarbonylamino)-3-phenylpent-4-enoic acid

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Technology Process of (2R,3S)-2-(benzyloxycarbonylamino)-3-phenylpent-4-enoic acid

There total 9 articles about (2R,3S)-2-(benzyloxycarbonylamino)-3-phenylpent-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:

: benzyl (2RS,3SR)-1-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-1-oxo-3-phenylpent-4-en-2-ylcarbamate

: (2S,3R)-2-(benzyloxycarbonylamino)-3-phenylpent-4-enoic acid

: 953787-40-1
(2R,3S)-2-(benzyloxycarbonylamino)-3-phenylpent-4-enoic acid

Guidance literature:: benzyl (2RS,3SR)-1-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-1-oxo-3-phenylpent-4-en-2-ylcarbamate; With lithium (hydro)trimethoxyaluminate; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

With sodium chlorite; 2-methyl-but-2-ene; acetic acid; In tetrahydrofuran; water; tert-butyl alcohol; at 10 - 20 ℃; Further stages. Title compound not separated from byproducts.;
DOI:10.1021/ol701704h

Reference yield:

: 85669-63-2
(E)-cinnamyl diethyl phosphate

: 953787-40-1
(2R,3S)-2-(benzyloxycarbonylamino)-3-phenylpent-4-enoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: chiral bidentate phosphite-type ligand / [Ir(cod)Cl]2 / tetrahydrofuran / 0.17 h / 20 °C

1.2: LiN(SiMe₃)2 / tetrahydrofuran / 0 °C

2.1: citric acid / tetrahydrofuran; H₂O / 4 h / 20 °C

3.1: TFA / CH₂Cl₂ / 3 h / 20 °C

4.1: NaOH / H₂O / 1 h / 0 °C

With sodium hydroxide; chiral bidentate phosphite-type ligand; trifluoroacetic acid; citric acid; bis(1,5-cyclooctadiene)diiridium(I) dichloride; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo034638f

Reference yield:

: benzyl (2RS,3SR)-1-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-1-oxo-3-phenylpent-4-en-2-ylcarbamate

: (2S,3R)-2-(benzyloxycarbonylamino)-3-phenylpent-4-enoic acid

: 2-(benzyloxycarbonylamino)-3-phenylpent-4-enoic acid

: 953787-40-1
(2R,3S)-2-(benzyloxycarbonylamino)-3-phenylpent-4-enoic acid

Guidance literature:: benzyl (2RS,3SR)-1-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-1-oxo-3-phenylpent-4-en-2-ylcarbamate; With iodine; In tetrahydrofuran; water; at 20 ℃; for 3h;

With acetic acid; zinc; at 65 ℃; for 2h; Further stages. Title compound not separated from byproducts.;
DOI:10.1021/ol701704h