Kalkitoxin

Base Information

• Chemical Name: Kalkitoxin
• CAS No.: 247184-89-0
• Molecular Formula: C21H38N2OS
• Molecular Weight: 366.60400
• UNII: 79JC6ZX2R6
• DSSTox Substance ID: DTXSID80897233
• Nikkaji Number: J1.488.072K
• Wikipedia: Kalkitoxin
• Wikidata: Q27266756
• Metabolomics Workbench ID: 103514
• Mol file: 247184-89-0.mol

Synonyms:kalkitoxin

Chemical Property of Kalkitoxin

Chemical Property:

• PSA: 57.97000
• LogP: 4.70500
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 366.27048501
• Heavy Atom Count: 25
• Complexity: 463

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Chemical Classes: other linear non-peptide (Lyngbya toxin (alkaloid))
• Canonical SMILES: CCC(C)C(=O)N(C)CCC(C)CC(C)C(C)CC1=NC(CS1)C=C
• Isomeric SMILES: CC[C@@H](C)C(=O)N(C)CC[C@@H](C)C[C@H](C)[C@H](C)CC1=N[C@@H](CS1)C=C

Technology Process of Kalkitoxin

There total 205 articles about Kalkitoxin 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: 84.0%

(S)-N-[(3R,5R,6S)-7-((R)-1-Hydroxymethyl-allylthiocarbamoyl)-3,5,6-trimethyl-heptyl]-2,N-dimethyl-butyramide (756900-29-5) → (+)-(3R,7S,8R,10R,2'S)-kalkitoxin (247184-89-0)

Guidance literature:

With 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; at -20 ℃; for 0.5h;

DOI:10.1016/j.tet.2004.06.014

Reference yield: 81.0%

N-((2R)-3-butenol-2-yl)-[(3R,4S,6S)-trimethyl-8-((2R)-N-methyl-2-methylbutyramido)]octanethioamide (320742-86-7) → (+)-kalkitoxin (247184-89-0)

Guidance literature:

With 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; at -20 ℃; for 0.5h;

DOI:10.1021/ja005526y DOI:10.1016/j.tet.2004.06.014

Reference yield: 67.0%

(1''R,2'R,3R,4S,6S)-3,4,6-trimethyl-8-[methyl-(2'-methylbutyryl)amino]octanoic acid (1''-mercaptomethylallyl)amide (619328-43-7) → (+)-kalkitoxin (247184-89-0)

Guidance literature:

With titanium tetrachloride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1039/b404205k

upstream raw materials:

(S)-2-Methylbutyric acid

(3S,4S,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene

(3R,5R)-3,5-dimethyl-6-(tert-butyldiphenylsilyloxy)hexanol

(2S)-N-methyl-N-((3R,5R)-3,5-dimethyl-6-hydroxy-hex-1-yl)-2-methylbutyramide

Refernces

• 1、 Umezawa, Taiki,Sueda, Manabu,Kamura, Takao,Kawahara, Teppei,Han, Xuerong,Okino, Tatsufumi,Matsuda, Fuyuhiko. "Synthesis and biological activity of kalkitoxin and its analogues". . p. 357 - 370. Retrieved 2012/02/15.
• 2、 White, James D.,Xu, Qing,Lee, Chang-Sun,Valeriote, Frederick A.. "Total synthesis and biological evaluation of (+)-kalkitoxin, a cytotoxic metabolite of the cyanobacterium Lyngbya majuscula". . p. 2092 - 2102. Retrieved 2007/10/03.