3-((3S,5S)-1,5-bis(benzyloxycarbonyl)pyrrolidin-3-yl)-1-methyl-3H-1,2,3-triazol-1-ium iodide

Base Information

• Chemical Name: 3-((3S,5S)-1,5-bis(benzyloxycarbonyl)pyrrolidin-3-yl)-1-methyl-3H-1,2,3-triazol-1-ium iodide
• CAS No.: 1279110-14-3
• Molecular Formula: C₂₃H₂₅N₄O₄*I
• Molecular Weight: 548.38
• Mol file: 1279110-14-3.mol

Synonyms:3-((3S,5S)-1,5-bis(benzyloxycarbonyl)pyrrolidin-3-yl)-1-methyl-3H-1,2,3-triazol-1-ium iodide

Chemical Property of 3-((3S,5S)-1,5-bis(benzyloxycarbonyl)pyrrolidin-3-yl)-1-methyl-3H-1,2,3-triazol-1-ium iodide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((3S,5S)-1,5-bis(benzyloxycarbonyl)pyrrolidin-3-yl)-1-methyl-3H-1,2,3-triazol-1-ium iodide

There total 3 articles about 3-((3S,5S)-1,5-bis(benzyloxycarbonyl)pyrrolidin-3-yl)-1-methyl-3H-1,2,3-triazol-1-ium iodide 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: 97.0%

dibenzyl (2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate (1279110-13-2) + methyl iodide (74-88-4) → 3-((3S,5S)-1,5-bis(benzyloxycarbonyl)pyrrolidin-3-yl)-1-methyl-3H-1,2,3-triazol-1-ium iodide (1279110-14-3)

Guidance literature:

In acetonitrile; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2011.01.031

Reference yield:

dibenzyl (2S,4S)-4-(4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate (1279110-12-1) → 3-((3S,5S)-1,5-bis(benzyloxycarbonyl)pyrrolidin-3-yl)-1-methyl-3H-1,2,3-triazol-1-ium iodide (1279110-14-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C

2: acetonitrile / Inert atmosphere; Reflux

With tetrabutyl ammonium fluoride; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.tet.2011.01.031

Reference yield:

(2S,4S)-Nα-Cbz-4-azidoproline benzyl ester (329191-55-1) → 3-((3S,5S)-1,5-bis(benzyloxycarbonyl)pyrrolidin-3-yl)-1-methyl-3H-1,2,3-triazol-1-ium iodide (1279110-14-3)

Guidance literature:

Multi-step reaction with 3 steps

1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 20 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C

3: acetonitrile / Inert atmosphere; Reflux

With tetrabutyl ammonium fluoride; copper(II) sulfate; sodium L-ascorbate; In tetrahydrofuran; water; acetonitrile; tert-butyl alcohol;

DOI:10.1016/j.tet.2011.01.031

upstream raw materials:

dibenzyl (2S,4S)-4-(4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate

dibenzyl (2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate

methyl iodide

(2S,4S)-N^α-Cbz-4-azidoproline benzyl ester