Aguerin B

Base Information

• Chemical Name: Aguerin B
• CAS No.: 68370-45-6
• Molecular Formula: C19H22O5
• Molecular Weight: 330.38
• DSSTox Substance ID: DTXSID20987920
• Nikkaji Number: J20.237A
• Wikidata: Q82976293
• Metabolomics Workbench ID: 141964
• ChEMBL ID: CHEMBL520721
• Mol file: 68370-45-6.mol

Synonyms:aguerin B

Chemical Property of Aguerin B

Chemical Property:

• PSA: 72.83000
• LogP: 2.08520
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 330.14672380
• Heavy Atom Count: 24
• Complexity: 673

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C(=O)OC1CC(=C)C2CC(C(=C)C2C3C1C(=C)C(=O)O3)O
• Isomeric SMILES: CC(=C)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@@H](C(=C)[C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)O

Technology Process of Aguerin B

There total 3 articles about Aguerin B 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: 89.0%

(1R,3S,5R,6R,7R,8S)-3-(methoxymethoxy)-13,14,15-trimethylene-12-oxododecahydroazuleno[6,7-β]furan-8-yl methacrylate (1549718-98-0) → aguerin B (68370-45-6)

Guidance literature:

With pyridinium p-toluenesulfonate; In tert-butyl alcohol; for 26h; Inert atmosphere; Reflux;

DOI:10.1016/j.bmcl.2013.12.099

Reference yield:

cynaporicrin (35932-39-9,35730-78-0) → aguerin B (68370-45-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 19 h / 0 °C / Reflux; Inert atmosphere

2.1: sodium hydroxide; water / 28 h / 20 °C

3.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 0.5 h / 20 °C / Inert atmosphere

3.2: 7.5 h / Reflux; Inert atmosphere

4.1: pyridinium p-toluenesulfonate / tert-butyl alcohol / 26 h / Inert atmosphere; Reflux

With 2,4,6-trichlorobenzoyl chloride; water; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2013.12.099

Reference yield:

(1R,3S,5R,6R,7R,8S)-3-(methoxymethoxy)-13,14,15-trimethylene-12-oxododecahydroazuleno[6,7-β]furan-4-yl 17-((methoxymethoxy)methyl)acrylate (1549718-80-0) → aguerin B (68370-45-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide; water / 28 h / 20 °C

2.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 0.5 h / 20 °C / Inert atmosphere

2.2: 7.5 h / Reflux; Inert atmosphere

3.1: pyridinium p-toluenesulfonate / tert-butyl alcohol / 26 h / Inert atmosphere; Reflux

With 2,4,6-trichlorobenzoyl chloride; water; pyridinium p-toluenesulfonate; triethylamine; sodium hydroxide; In toluene; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2013.12.099

upstream raw materials:

cynaporicrin

(1R,3S,5R,6R,7R,8S)-3-(methoxymethoxy)-13,14,15-trimethylene-12-oxododecahydroazuleno[6,7-β]furan-4-yl 17-((methoxymethoxy)methyl)acrylate

(1R,3S,5R,6R,7R,8S)-3-(methoxymethoxy)-13,14,15-trimethylene-12-oxododecahydroazuleno[6,7-β]furan-8-yl methacrylate

Downstream raw materials:

(4S,6aR,8S,9bR)-4,8-Dihydroxy-3,6,9-trimethylene-decahydro-azuleno[4,5-b]furan-2-one

Refernces