Kendomycin

Base Information

• Chemical Name: Kendomycin
• CAS No.: 183202-73-5
• Molecular Formula: C₂₉H₄₂O₆
• Molecular Weight: 486.649
• NSC Number: 716244
• DSSTox Substance ID: DTXSID901043890
• Nikkaji Number: J2.148.493H
• Wikipedia: Kendomycin
• Wikidata: Q262602
• Metabolomics Workbench ID: 111525
• ChEMBL ID: CHEMBL523927
• Mol file: 183202-73-5.mol

Synonyms:kendomycin;TAN 2162;TAN-2162;TAN2162

Chemical Property of Kendomycin

Chemical Property:

• Melting Point: 236-240℃
• Refractive Index: 1.626
• PSA: 96.22000
• Density: 1.43g/cm³
• LogP: 5.12950
• Storage Temp.: −20°C
• XLogP3: 4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 486.29813906
• Heavy Atom Count: 35
• Complexity: 1000

Purity/Quality:

98% ^*data from raw suppliers

Kendomycin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2C(C(C(C(O2)C3=C(C(=O)C(=C4C3=CC(O4)(C(CC(CC(=C1)C)C)C)O)C)O)C)O)C
• Isomeric SMILES: C[C@H]\1CC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)C3=C(C(=O)C(=C4C3=C[C@@](O4)([C@H](C[C@@H](C/C(=C1)/C)C)C)O)C)O)C)O)C
• Description: Kendomycin is a macrolide from Streptomyces which displays potent cytotoxicity against several carcinoma cell lines (GI50 < 100 nM). It also acts as an endothelin receptor antagonist and has antiosteoporotic activities. Certain effects are thought to be mediated through inhibition of proteasomal degradation of proteins.
• Uses: Kendomycin is an unusual macrocyclic metabolite containing a rare quinone methide group. Kendomycin is a potent antibacterial agent against Gram positive and Gram negative bacteria, including MRSA strains, also displaying antitumour activity. Kendomycin is a potent endothelin receptor agonist and demonstrates antiosteoporotic activity. Kendomycin is a broadly efficacious polyketide macrocycle antibiotic.

Technology Process of Kendomycin

There total 128 articles about Kendomycin 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: 91.0%

C35H56O6Si (1220044-85-8) → (5R,6R,7S,8R,9R,12S,13E,16S,18S,19S)-6,7,8,9,10,11,12,15,16,17,18,19-dodecahydro-4,7,19-trihydroxy-2,6,8,12,14,16,18-heptamethyl-1,19:5,9-diepoxybenzo[18]annulen-3(5H)-one (183202-73-5)

Guidance literature:

With hydrogen fluoride; In water; acetonitrile; at 0 - 20 ℃;

DOI:10.1021/ol100229f

Reference yield: 68.0%

(E)-(1R,10S,12S,16S,19R,20S,21S,22S)-21-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-5,10,12,14,16,20,22-heptamethyl-23-oxa-tricyclo[17.3.1.02,7]tricosa-2(7),5,14-triene-3,4,9-trione (853995-85-4) → C35H56O6Si + (5R,6R,7S,8R,9R,12S,13E,16S,18S,19S)-6,7,8,9,10,11,12,15,16,17,18,19-dodecahydro-4,7,19-trihydroxy-2,6,8,12,14,16,18-heptamethyl-1,19:5,9-diepoxybenzo[18]annulen-3(5H)-one (183202-73-5)

Guidance literature:

With hydrogen fluoride; water; In acetonitrile; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol801499s

Reference yield: 50.0%

C35H54O5Si (808766-09-8) → (5R,6R,7S,8R,9R,12S,13E,16S,18S,19S)-6,7,8,9,10,11,12,15,16,17,18,19-dodecahydro-4,7,19-trihydroxy-2,6,8,12,14,16,18-heptamethyl-1,19:5,9-diepoxybenzo[18]annulen-3(5H)-one (183202-73-5)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 20 ℃;

DOI:10.1021/ja0447154

upstream raw materials:

C₃₅H₅₄O₅Si

(E)-(1R,10S,12S,16S,19R,20S,21S,22S)-21-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-5,10,12,14,16,20,22-heptamethyl-23-oxa-tricyclo[17.3.1.0^2,7]tricosa-2⁽⁷⁾,5,14-triene-3,4,9-trione

(2S,3R,6S)-3-Hydroxy-2,6-dimethyl-oct-7-enoic acid

2-bromo-6-hydroxy-3,5-dimethoxy-4-methyl-benzaldehyde