(5S,7E,9E,11Z,14Z,17Z)-6-[(2R)-2-amino-3-(carboxymethylamino)-3-oxopropyl]sulfanyl-5-hydroxyicosa-7,9,11,14,17-pentaenoic acid

Base Information

• Chemical Name: (5S,7E,9E,11Z,14Z,17Z)-6-[(2R)-2-amino-3-(carboxymethylamino)-3-oxopropyl]sulfanyl-5-hydroxyicosa-7,9,11,14,17-pentaenoic acid
• CAS No.: 79695-13-9
• Molecular Formula: C₂₅H₃₈N₂O₆S
• Molecular Weight: 494.653
• Mol file: 79695-13-9.mol

Synonyms:79695-13-9;(5S,7E,9E,11Z,14Z,17Z)-6-[(2R)-2-amino-3-(carboxymethylamino)-3-oxopropyl]sulfanyl-5-hydroxyicosa-7,9,11,14,17-pentaenoic acid;Glycine, S-((1R,2E,4E,6Z,9Z,12Z)-1-((1S)-4-carboxy-1-hydroxybutyl)-2,4,6,9,12-pentadecapentaenyl)-L-cysteinyl-;C25H38N2O6S;C25-H38-N2-O6-S

Chemical Property of (5S,7E,9E,11Z,14Z,17Z)-6-[(2R)-2-amino-3-(carboxymethylamino)-3-oxopropyl]sulfanyl-5-hydroxyicosa-7,9,11,14,17-pentaenoic acid

Chemical Property:

• Vapor Pressure: 9.12E-29mmHg at 25°C
• Boiling Point: 788.9°C at 760 mmHg
• Flash Point: 430.9°C
• PSA: 175.25000
• Density: 1.175g/cm³
• LogP: 4.29450
• Storage Temp.: −70°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 19
• Exact Mass: 494.24505811
• Heavy Atom Count: 34
• Complexity: 746

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Hazard Codes: F,T
• Statements: 11
• Safety Statements: 7-16-23-45

MSDS Files:

Useful:

• Canonical SMILES: CCC=CCC=CCC=CC=CC=CC(C(CCCC(=O)O)O)SCC(C(=O)NCC(=O)O)N
• Isomeric SMILES: CC/C=C\C/C=C\C/C=C\C=C\C=C\C([C@H](CCCC(=O)O)O)SC[C@@H](C(=O)NCC(=O)O)N

Technology Process of (5S,7E,9E,11Z,14Z,17Z)-6-[(2R)-2-amino-3-(carboxymethylamino)-3-oxopropyl]sulfanyl-5-hydroxyicosa-7,9,11,14,17-pentaenoic acid

There total 9 articles about (5S,7E,9E,11Z,14Z,17Z)-6-[(2R)-2-amino-3-(carboxymethylamino)-3-oxopropyl]sulfanyl-5-hydroxyicosa-7,9,11,14,17-pentaenoic 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:

1-bromo-pent-2-yne (16400-32-1) → LTD5 (79695-13-9)

Guidance literature:

Multi-step reaction with 8 steps

1: DBU, CuI, HMPT / tetrahydrofuran

2: H₂, (C₂H₅)N / Lindlar catalyst / tetrahydrofuran

3: CBr₄, P(C₆H₅)3 / CH₂Cl₂ / 0.17 h / 0 °C

4: acetonitrile / Heating

5: BuLi, HMPT / tetrahydrofuran / -78 °C

6: 30 percent / 0.08 h / -78 °C

7: 60 percent

8: 0.1 M K₂CO₃ aq. / 12 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; n-butyllithium; carbon tetrabromide; (C₂H₅)N; hydrogen; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/ardp.19843170317

Reference yield:

nona-3,6-diyn-1-ol (57386-91-1) → LTD5 (79695-13-9)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂, (C₂H₅)N / Lindlar catalyst / tetrahydrofuran

2: CBr₄, P(C₆H₅)3 / CH₂Cl₂ / 0.17 h / 0 °C

3: acetonitrile / Heating

4: BuLi, HMPT / tetrahydrofuran / -78 °C

5: 30 percent / 0.08 h / -78 °C

6: 60 percent

7: 0.1 M K₂CO₃ aq. / 12 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; carbon tetrabromide; (C₂H₅)N; hydrogen; potassium carbonate; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/ardp.19843170317

Reference yield:

(Z,Z)-1-hydroxynona-3,6-diene (53046-97-2,167820-65-7,53250-56-9) → LTD5 (79695-13-9)

Guidance literature:

Multi-step reaction with 6 steps

1: CBr₄, P(C₆H₅)3 / CH₂Cl₂ / 0.17 h / 0 °C

2: acetonitrile / Heating

3: BuLi, HMPT / tetrahydrofuran / -78 °C

4: 30 percent / 0.08 h / -78 °C

5: 60 percent

6: 0.1 M K₂CO₃ aq. / 12 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; carbon tetrabromide; potassium carbonate; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/ardp.19843170317

upstream raw materials:

1-bromo-pent-2-yne

cysteinylglycine

nona-3,6-diyn-1-ol

(Z,Z)-1-hydroxynona-3,6-diene

Refernces