6-Eicosenoic acid, 2-amino-3,4,5-trihydroxy-2-methyl-14-oxo-

Base Information

• Chemical Name: 6-Eicosenoic acid, 2-amino-3,4,5-trihydroxy-2-methyl-14-oxo-
• CAS No.: 145401-48-5
• Molecular Formula: C₂₁H₃₉NO₆
• Molecular Weight: 401.544
• Nikkaji Number: J519.109B
• Mol file: 145401-48-5.mol

Synonyms:sphingofungin F

Chemical Property of 6-Eicosenoic acid, 2-amino-3,4,5-trihydroxy-2-methyl-14-oxo-

Chemical Property:

• Vapor Pressure: 1.31E-18mmHg at 25°C
• Melting Point: 145-147 °C
• Boiling Point: 631.6°C at 760 mmHg
• PKA: 2.21±0.50(Predicted)
• Flash Point: 335.8°C
• PSA: 141.08000
• Density: 1.121g/cm³
• LogP: 3.00770
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 17
• Exact Mass: 401.27773796
• Heavy Atom Count: 28
• Complexity: 482

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC(=O)CCCCCCC=CC(C(C(C(C)(C(=O)O)N)O)O)O
• Isomeric SMILES: CCCCCCC(=O)CCCCCC/C=C/C(C(C(C(C)(C(=O)O)N)O)O)O

Technology Process of 6-Eicosenoic acid, 2-amino-3,4,5-trihydroxy-2-methyl-14-oxo-

There total 92 articles about 6-Eicosenoic acid, 2-amino-3,4,5-trihydroxy-2-methyl-14-oxo- 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: 98.0%

N-((3S,4R,5R)-4-hydroxy-5-((S,E)-1-hydroxy-10-oxohexadec-2-en-1-yl)-3-methyl-2-oxotetrahydrofuran-3-yl)acetamide → sphingofungin F (145401-48-5)

Guidance literature:

With sodium hydroxide; In methanol; water; at 65 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b00475

Reference yield: 79.0%

C28H39NO5 → sphingofungin F (145401-48-5)

Guidance literature:

With sodium hydroxide; water; In water; at 20 ℃; for 24h;

DOI:10.1021/ol020164f

Reference yield: 72.0%

(2S,3S,4R,5S)-2-amino-4-benzyloxy-2-methyl-3,5-dihydroxy-14-oxoeicos-6-enoic acid (189246-66-0) → sphingofungin F (145401-48-5)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 ℃;

DOI:10.1055/s-1997-783

upstream raw materials:

(2S,3S,4R,5S)-2-amino-4-benzyloxy-2-methyl-3,5-dihydroxy-14-oxoeicos-6-enoic acid

N-[(3S,4R,5R)-4-Hydroxy-5-((E)-(S)-1-hydroxy-10-oxo-hexadec-2-enyl)-3-methyl-2-oxo-tetrahydro-furan-3-yl]-benzamide

(4S,5R,1'R,2'S,3'E)-4-methyl-5-(1',2'-dihydroxy-11'-ketoheptadec-3'-enyl)-2-oxazolidinone-1-carboxylic acid γ-lactone

6-[1-(tert-butyl-dimethyl-silanyloxy)-9-(2-hexyl-[1,3]dioxolan-2-yl)-non-2-enyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

Refernces

• 1、 Li, Min,Wu, Anmei. "Total synthesis of sphingofungin F". . p. 2985 - 2988. Retrieved 2006.
• 2、 Gan, Feng-Feng,Yang, Shao-Bo,Luo, Yong-Chun,Yang, Wan-Bang,Xu, Peng-Fei. "Total Synthesis of Sphingofungin F Based on Chiral Tricyclic Iminolactone". experimental part. p. 2737 - 2740. Retrieved 2010/07/08.