(2E,4E)-N-[(2S,3R)-3-hydroxy-1-[[(3Z,5S,8S,10S)-10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl]amino]-1-oxobutan-2-yl]dodeca-2,4-dienamide

Base Information

• Chemical Name: (2E,4E)-N-[(2S,3R)-3-hydroxy-1-[[(3Z,5S,8S,10S)-10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl]amino]-1-oxobutan-2-yl]dodeca-2,4-dienamide
• CAS No.: 108351-50-4
• Molecular Formula: C₂₇H₄₄N₄O₆
• Molecular Weight: 520.67
• Wikidata: Q27460680
• ChEMBL ID: CHEMBL1233002
• Mol file: 108351-50-4.mol

Synonyms:CHEMBL1233002;SCHEMBL13088013;obutan-2-yl]dodeca-2,4-dienamide;(2E,4E)-N-[(2S,3R)-3-hydroxy-1-[[(3Z,5S,8S,10S)-10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl]amino]-1-oxobutan-2-yl]dodeca-2,4-dienamide;Q27460680;(2E,4E)-N-[(2S,3R)-3-hydroxy-1-[[(3Z,5S,8S,10S)-10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl]amino]-1-ox

Chemical Property of (2E,4E)-N-[(2S,3R)-3-hydroxy-1-[[(3Z,5S,8S,10S)-10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl]amino]-1-oxobutan-2-yl]dodeca-2,4-dienamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 892.9°Cat760mmHg
• Flash Point: 493.8°C
• PSA: 170.82000
• Density: 1.16g/cm³
• LogP: 3.37390
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 520.32608514
• Heavy Atom Count: 37
• Complexity: 826

Purity/Quality:

95% ^*data from raw suppliers

GLIDOBACTIN A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCC=CC=CC(=O)NC(C(C)O)C(=O)NC1CC(CCNC(=O)C=CC(NC1=O)C)O
• Isomeric SMILES: CCCCCCC/C=C/C=C/C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@H]1C[C@H](CCNC(=O)/C=C/[C@@H](NC1=O)C)O

Technology Process of (2E,4E)-N-[(2S,3R)-3-hydroxy-1-[[(3Z,5S,8S,10S)-10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl]amino]-1-oxobutan-2-yl]dodeca-2,4-dienamide

There total 22 articles about (2E,4E)-N-[(2S,3R)-3-hydroxy-1-[[(3Z,5S,8S,10S)-10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl]amino]-1-oxobutan-2-yl]dodeca-2,4-dienamide 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: 100.0%

(2E,4E)-Dodeca-2,4-dienoic acid [(1S,2R)-2-hydroxy-1-((E)-(5S,8S,10S)-10-methoxymethoxy-5-methyl-2,7-dioxo-1,6-diaza-cyclododec-3-en-8-ylcarbamoyl)-propyl]-amide (145958-14-1) → glidobactin A (108351-50-4)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; at 0 ℃; for 6h;

DOI:10.1039/c39920001687

Reference yield:

((2E,4E)-dodeca-2,4-dienoyl)-(L)-threonine + (5S,8S,10S,E)-8-amino-10-hydroxy-5-methyl-1,6-diazacyclododec-3-ene-2,7-dione → glidobactin A (108351-50-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 12h;

DOI:10.1016/j.chembiol.2020.07.012

Reference yield:

di-tert-butyl ((3S,5S)-3-hydroxy-6-oxo-6-(((S)-1-oxopropan-2-yl)amino)hexane-1,5-diyl)dicarbamate → glidobactin A (108351-50-4)

Guidance literature:

Multi-step reaction with 4 steps

1: acetonitrile / 2 h / 60 °C

2: chlorotriisopropylsilane; phenol / water / 20 °C

3: 4‐(4,6dimethoxy‐1,3,5‐triazin‐2‐yl)‐4‐methylmorpholinium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 36 h / 20 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide / 12 h / 0 - 20 °C

With 4‐(4,6dimethoxy‐1,3,5‐triazin‐2‐yl)‐4‐methylmorpholinium tetrafluoroborate; chlorotriisopropylsilane; N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; phenol; In water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.chembiol.2020.07.012

upstream raw materials:

2(E),4(E)-dodecadienoic acid succinimido ester

(2E,4E)-Dodeca-2,4-dienoic acid [(1S,2R)-2-hydroxy-1-((E)-(5S,8S,10S)-10-methoxymethoxy-5-methyl-2,7-dioxo-1,6-diaza-cyclododec-3-en-8-ylcarbamoyl)-propyl]-amide

((E)-(5S,8S,10S)-10-Methoxymethoxy-5-methyl-2,7-dioxo-1,6-diaza-cyclododec-3-en-8-yl)-carbamic acid tert-butyl ester

[(1S,2R)-2-Hydroxy-1-((E)-(5S,8S,10S)-10-methoxymethoxy-5-methyl-2,7-dioxo-1,6-diaza-cyclododec-3-en-8-ylcarbamoyl)-propyl]-carbamic acid tert-butyl ester