(S)-methyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-bis-(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate

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Chemical Name:(S)-methyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-bis-(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate
CAS No.:1355611-42-5
Molecular Formula:C₂₃H₃₂N₂O₆S
Molecular Weight:464.583
Hs Code.:

Synonyms:(S)-methyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-bis-(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate

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Chemical Property of (S)-methyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-bis-(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate

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Technology Process of (S)-methyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-bis-(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate

There total 4 articles about (S)-methyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-bis-(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate 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: 64.0%

: 1117-71-1
methyl 4-bromocrotonate

: 1355611-21-0
benzyl (2-((2S,5S)-2,5-bis(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)carbamate

: 1355611-42-5
(S)-methyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-bis-(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate

Guidance literature:: methyl 4-bromocrotonate; benzyl (2-((2S,5S)-2,5-bis(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)carbamate; With ferric(III) bromide; In acetonitrile; at 45 - 50 ℃; Inert atmosphere;

With triethylamine; In tetrahydrofuran; acetonitrile; at -78 - 45 ℃; optical yield given as %de; diastereoselective reaction;
DOI:10.1021/jo201753q

Reference yield:

: 1355611-18-5
C₁₈H₂₆N₂O₅

: 1355611-42-5
(S)-methyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-bis-(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate

Guidance literature:: Multi-step reaction with 2 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

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

Reference yield:

: 1138-80-3
N-(Benzyloxycarbonyl)glycine

: 1355611-42-5
(S)-methyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-bis-(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: dmap; triethylamine; dicyclohexyl-carbodiimide

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

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

3.2: -78 - 45 °C

With Lawessons reagent; dmap; ferric(III) bromide; sodium hydrogencarbonate; triethylamine; dicyclohexyl-carbodiimide; In toluene; acetonitrile; 3.2: thio-Claisen rearrangement;
DOI:10.1021/jo201753q