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

Base Information

• Chemical Name: (S)-ethyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-bis-(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate
• CAS No.: 1355611-45-8
• Molecular Formula: C₂₄H₃₄N₂O₆S
• Molecular Weight: 478.61
• Mol file: 1355611-45-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-ethyl 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)-ethyl 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: 65.0%

4-bromocrotonic ethyl ester (6065-32-3) + benzyl (2-((2S,5S)-2,5-bis(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)carbamate (1355611-21-0) → (S)-ethyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-bis-(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate (1355611-45-8)

Guidance literature:

4-bromocrotonic ethyl ester; 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:

C18H26N2O5 (1355611-18-5) → (S)-ethyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-bis-(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate (1355611-45-8)

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:

N-(Benzyloxycarbonyl)glycine (1138-80-3) → (S)-ethyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2S,5S)-2,5-bis-(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate (1355611-45-8)

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

upstream raw materials:

4-bromocrotonic ethyl ester

benzyl (2-((2S,5S)-2,5-bis(methoxymethyl)pyrrolidin-1-yl)-2-thioxoethyl)carbamate

C₁₈H₂₆N₂O₅

(2S,5S)-2,5-bis(methoxymethyl)pyrrolidine

Downstream raw materials:

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