Zaragozic acid A

Base Information

• Chemical Name: Zaragozic acid A
• CAS No.: 142561-96-4
• Molecular Formula: C₃₅H₄₆O₁₄
• Molecular Weight: 690.742
• UNII: 1117HVX02L
• DSSTox Substance ID: DTXSID701018091
• Nikkaji Number: J513.990B
• Wikipedia: Zaragozic_acid
• Wikidata: Q8066579
• Pharos Ligand ID: GDRHYK3ADWVS
• Metabolomics Workbench ID: 21261
• ChEMBL ID: CHEMBL280978
• Mol file: 142561-96-4.mol

Synonyms:7-deoxy zaragozic acid;squalestatin;squalestatin 1;squalestatin s1;zaragozic acid A

Chemical Property of Zaragozic acid A

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 850.1 ºC
• PKA: 1.47±0.70(Predicted)
• Flash Point: 260.9 ºC
• PSA: 217.35000
• Density: 1.35 g/cm³⁸
• LogP: 4.87800
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 19
• Exact Mass: 690.28875614
• Heavy Atom Count: 49
• Complexity: 1290

Purity/Quality:

98%Min ^*data from raw suppliers

ZaragozicAcidA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)CC(C)C=CC(=O)OC1C(C2(OC(C(C1(O2)C(=O)O)(C(=O)O)O)C(=O)O)CCC(=C)C(C(C)CC3=CC=CC=C3)OC(=O)C)O
• Isomeric SMILES: CC[C@H](C)C[C@H](C)/C=C/C(=O)O[C@@H]1[C@H]([C@]2(O[C@@H]([C@]([C@@]1(O2)C(=O)O)(C(=O)O)O)C(=O)O)CCC(=C)[C@H]([C@H](C)CC3=CC=CC=C3)OC(=O)C)O
• Uses: Zaragozic acid A is the major metabolite of a class of unusual bicyclic tricarboxylic acids, produced by a number of fungi in the genera Curvularia, Exserohilum, Setosphaeria and others, discovered at Merck and Glaxo in the early 1990s. In nature, zaragozic acid A acts as broad spectrum antifungal but its mode of action as an inhibitor of squalene synthase, involved in sterol biosynthesis, lead to investigation as a cholesterol lowering agent. Zaragozic acid A prepared by BioAustralis is presented as the free acid rather than the tri-sodium salt to avoid stability problems associated with hydrolysis of the salt.

Technology Process of Zaragozic acid A

There total 25 articles about Zaragozic acid A 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: 90.0%

tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,6(2E,4S,6S),7R]-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-6-(4,6-dimethyl-2-octenoyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate (925453-77-6) → zaragozic acid A (138682-84-5,144786-97-0,146075-86-7,148152-80-1,149656-40-6,142561-96-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 16h;

DOI:10.1002/chem.200601212

Reference yield: 74.0%

<1S-<1α(4R*,5R*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 3,4,5-tris(1,1-dimethylethyl) ester (144358-24-7) → zaragozic acid A (138682-84-5,144786-97-0,146075-86-7,148152-80-1,149656-40-6,142561-96-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 11h; Ambient temperature;

DOI:10.1021/jo961533m

Reference yield: 50.0%

<5(2E,4S,6S),7S>-2,7-Anhydro-8,9,10,12,13-pentadeoxy-11-ethanoate-10-methylene-3,4-bis-C-<(phenylmethoxy)carbonyl>-12-(phenylmethyl)-5-(4,6-dimethyl-2-octenoate)-L-erythro-L-glycero-D-altro-7-trideculo-7,4-furanosonic acid phenylmethyl ester (146008-35-7) → zaragozic acid A (138682-84-5,144786-97-0,146075-86-7,148152-80-1,149656-40-6,142561-96-4)

Guidance literature:

With cyclohexa-1,4-diene; hydrogen; palladium on activated charcoal; In 1,4-dioxane; at 110 ℃; for 2h;

upstream raw materials:

<5(2E,4S,6S),7S>-2,7-Anhydro-8,9,10,12,13-pentadeoxy-11-ethanoate-10-methylene-3,4-bis-C-<(phenylmethoxy)carbonyl>-12-(phenylmethyl)-5-(4,6-dimethyl-2-octenoate)-L-erythro-L-glycero-D-altro-7-trideculo-7,4-furanosonic acid phenylmethyl ester

<1S-<1α(4R*,5R*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 3,4,5-tris(1,1-dimethylethyl) ester

tri-tert-butyl [1S,1(4S,5R),3S,4S,5R,6R,6(2E,4S,6S),7R]-1-(4-acetoxy-5-methyl-3-methylene-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-6-(4,6-dimethyl-2-octenoyl)oxy-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

tri-tert-butyl [1S,1(3R,4S,5R),3S,4S,5R,6R,7R]-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-1-[4-hydroxy-3-(hydroxymethyl)-5-methyl-6-phenylhexyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

Downstream raw materials:

zaragozic acid A trimethyl ester

<1S-<1α(4R*,5R*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 3,4,5-tris(1,1-dimethylethyl) ester

(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tris-(2-trimethylsilanyl-ethyl) ester

(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3-benzyl ester