(2S,3S)-2-(benzyloxycarbonylamino)-3-(methoxycarbonyl)pent-4-enoic acid

Base Information

Chemical Name:(2S,3S)-2-(benzyloxycarbonylamino)-3-(methoxycarbonyl)pent-4-enoic acid
CAS No.:1355611-67-4
Molecular Formula:C₁₅H₁₇NO₆
Molecular Weight:307.303
Hs Code.:

Synonyms:(2S,3S)-2-(benzyloxycarbonylamino)-3-(methoxycarbonyl)pent-4-enoic acid

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Chemical Property of (2S,3S)-2-(benzyloxycarbonylamino)-3-(methoxycarbonyl)pent-4-enoic acid

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Technology Process of (2S,3S)-2-(benzyloxycarbonylamino)-3-(methoxycarbonyl)pent-4-enoic acid

There total 4 articles about (2S,3S)-2-(benzyloxycarbonylamino)-3-(methoxycarbonyl)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: 79.0%

: 1355611-38-9
(S)-methyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate

: 1355611-67-4
(2S,3S)-2-(benzyloxycarbonylamino)-3-(methoxycarbonyl)pent-4-enoic acid

Guidance literature:: (S)-methyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 - 20 ℃; for 1h;

With iodine; In tetrahydrofuran; water; at 20 ℃; for 96h; Darkness;

With acetic acid; zinc; at 70 ℃; for 2h; optical yield given as %ee;
DOI:10.1021/jo201753q

Reference yield:

: 953787-28-5
benzyl 2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-oxoethylcarbamate

: 1355611-67-4
(2S,3S)-2-(benzyloxycarbonylamino)-3-(methoxycarbonyl)pent-4-enoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: Lawessons reagent; sodium hydrogencarbonate / toluene / 3 h / 120 °C

2.1: ferric(III) bromide / acetonitrile / 45 - 50 °C / Inert atmosphere

2.2: -78 - 45 °C

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -78 - 20 °C

3.2: 96 h / 20 °C / Darkness

3.3: 2 h / 70 °C

With Lawessons reagent; ferric(III) bromide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene; acetonitrile; 2.2: thio-Claisen rearrangement;
DOI:10.1021/jo201753q

Reference yield:

: 1355611-20-9
benzyl (2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-thioxoethyl)-carbamate

: 1355611-67-4
(2S,3S)-2-(benzyloxycarbonylamino)-3-(methoxycarbonyl)pent-4-enoic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: ferric(III) bromide / acetonitrile / 45 - 50 °C / Inert atmosphere

1.2: -78 - 45 °C

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -78 - 20 °C

2.2: 96 h / 20 °C / Darkness

2.3: 2 h / 70 °C

With ferric(III) bromide; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile; 1.2: thio-Claisen rearrangement;
DOI:10.1021/jo201753q