Narbonolide

Base Information

• Chemical Name: Narbonolide
• CAS No.: 32885-75-9
• Molecular Formula: C20H32O5
• Molecular Weight: 0
• DSSTox Substance ID: DTXSID001043712
• Metabolomics Workbench ID: 70508
• Wikidata: Q27110204
• Mol file: 32885-75-9.mol

Synonyms:narbonolide

Chemical Property of Narbonolide

Chemical Property:

• PSA: 80.67000
• LogP: 2.94770
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 352.22497412
• Heavy Atom Count: 25
• Complexity: 524

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(C=CC(=O)C(CC(C(C(C(=O)C(C(=O)O1)C)C)O)C)C)C
• Isomeric SMILES: CC[C@@H]1[C@@H](/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H](C(=O)[C@H](C(=O)O1)C)C)O)C)C)C

Technology Process of Narbonolide

There total 12 articles about Narbonolide 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: 86.0%

(E)-(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione (918961-71-4) → narbonolide (32885-75-9)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1021/jo702384d

Reference yield:

(2R,3S,4S,6R,7R/S,8E,10R,11R)-S-2-acetamidoethyl-3,11-dihydroxy-2,4,6,10-tetramethyl-7-oxotridec-8-enethioate (858371-92-3) → narbonolide (32885-75-9)

Guidance literature:

With ethylenediaminetetraacetic acid; PikAIII; PikAIV; NADPH; In phosphate buffer; dimethyl sulfoxide; at 30 ℃; for 20h; pH=7.2; Further Variations:; Reagents; Enzyme kinetics;

DOI:10.1021/ja042592h

Reference yield:

C26H46O5Si → narbonolide (32885-75-9)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃;

DOI:10.1021/jo702384d

upstream raw materials:

(3S)-3-dihydronarbonolide

(2R,3S,4S,6R,7R/S,8E,10R,11R)-S-2-acetamidoethyl-3,11-dihydroxy-2,4,6,10-tetramethyl-7-oxotridec-8-enethioate

(E)-(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione

(E)-(2S,4R,8R,9R)-S-2-acetamidoethyl 9-hydroxy-2,4,8-trimethyl-5-oxoundec-6-enethioate

Downstream raw materials:

narbomycin

Refernces

• 1、 Chemler, Joseph A.,Coburn, Katherine M.,Hansen, Douglas A.,Koch, Aaron A.,Lowell, Andrew N.,Schmidt, Jennifer J.,Sherman, David H.. "Probing Selectivity and Creating Structural Diversity Through Hybrid Polyketide Synthases". . p. 13575 - 13580. Retrieved 2020.
• 2、 Aldrich, Courtney C.,Beck, Brian J.,Fecik, Robert A.,Sherman, David H.. "Biochemical investigation of pikromycin biosynthesis employing native penta- and hexaketide chain elongation intermediates". . p. 8441 - 8452. Retrieved 2005.
• 3、 Wu, Jiaquan,He, Weiguo,Khosla, Chaitan,Cane, David E.. "Chain elongation, macrolactonization, and hydrolysis of natural and reduced hexaketide substrates by the picromycin/methymycin polyketide synthase". . p. 7557 - 7560. Retrieved 2005.