(2S)-2-(benzoylamino)-3-{[(Z,4S)-1-(ethoxycarbonyl)-4-hydroxypent-1-enyl]thio}propanoic acid

Base Information

Chemical Name:(2S)-2-(benzoylamino)-3-{[(Z,4S)-1-(ethoxycarbonyl)-4-hydroxypent-1-enyl]thio}propanoic acid
CAS No.:288318-40-1
Molecular Formula:C₁₈H₂₃NO₆S
Molecular Weight:381.45
Hs Code.:

Synonyms:(2S)-2-(benzoylamino)-3-{[(Z,4S)-1-(ethoxycarbonyl)-4-hydroxypent-1-enyl]thio}propanoic acid

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Chemical Property of (2S)-2-(benzoylamino)-3-{[(Z,4S)-1-(ethoxycarbonyl)-4-hydroxypent-1-enyl]thio}propanoic acid

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Technology Process of (2S)-2-(benzoylamino)-3-{[(Z,4S)-1-(ethoxycarbonyl)-4-hydroxypent-1-enyl]thio}propanoic acid

There total 5 articles about (2S)-2-(benzoylamino)-3-{[(Z,4S)-1-(ethoxycarbonyl)-4-hydroxypent-1-enyl]thio}propanoic 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: 96.0%

: 288318-39-8
tert-butyl (2S)-2-(benzoylamino)-3-{[(4S)-1-(ethoxycarbonyl)-2-hydroxy-4-(methoxymethoxy)pentyl]thio}propanoate

: 288318-40-1
(2S)-2-(benzoylamino)-3-{[(Z,4S)-1-(ethoxycarbonyl)-4-hydroxypent-1-enyl]thio}propanoic acid

Guidance literature:: With cerium(III) chloride; sodium iodide; In acetonitrile; for 24h; Heating;
DOI:10.1021/jo000116d

Reference yield:

: 98-88-4
benzoyl chloride

: 288318-40-1
(2S)-2-(benzoylamino)-3-{[(Z,4S)-1-(ethoxycarbonyl)-4-hydroxypent-1-enyl]thio}propanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / pyridine / CH₂Cl₂ / 15 h / 0 - 20 °C

2: 70 percent / NaBH₄ / ethanol / 2 h / 25 °C

3: 86 percent / NaOCH₃ / methanol / 1 h / Heating

4: 65 percent / CeCl₂*7H₂O; t-BuMgCl / tetrahydrofuran / 6.5 h / -78 °C

5: 96 percent / CeCl₃*7H₂O; NaI / acetonitrile / 24 h / Heating

With pyridine; sodium tetrahydroborate; cerium(III) chloride; CeCl₂*7H₂O; tert-butylmagnesium chloride; sodium methylate; sodium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile; 1: Acylation / 2: reductive cleavage / 3: Alkylation / 4: Addition / 5: Hydrolysis;
DOI:10.1021/jo000116d

Reference yield:

: 73284-29-4
N-benzoyl-D-cystine di-tert-butyl ester

: 288318-40-1
(2S)-2-(benzoylamino)-3-{[(Z,4S)-1-(ethoxycarbonyl)-4-hydroxypent-1-enyl]thio}propanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 70 percent / NaBH₄ / ethanol / 2 h / 25 °C

2: 86 percent / NaOCH₃ / methanol / 1 h / Heating

3: 65 percent / CeCl₂*7H₂O; t-BuMgCl / tetrahydrofuran / 6.5 h / -78 °C

4: 96 percent / CeCl₃*7H₂O; NaI / acetonitrile / 24 h / Heating

With sodium tetrahydroborate; cerium(III) chloride; CeCl₂*7H₂O; tert-butylmagnesium chloride; sodium methylate; sodium iodide; In tetrahydrofuran; methanol; ethanol; acetonitrile; 1: reductive cleavage / 2: Alkylation / 3: Addition / 4: Hydrolysis;
DOI:10.1021/jo000116d