Veraguensin

Base Information

• Chemical Name: Veraguensin
• CAS No.: 19950-55-1
• Molecular Formula: C₂₂H₂₈O₅
• Molecular Weight: 372.461
• DSSTox Substance ID: DTXSID90332044
• Nikkaji Number: J15.498I
• Wikidata: Q27138010
• Metabolomics Workbench ID: 69602
• ChEMBL ID: CHEMBL4102990
• Mol file: 19950-55-1.mol

Synonyms:galbelgin;galgravin;galgravin, (2alpha,3alpha,4alpha,5alpha)-isomer;galgravin, (2alpha,3alpha,4alpha,5beta)-(+-)-isomer;galgravin, (2alpha,3alpha,4alpha,5beta)-isomer;galgravin, (2alpha,3alpha,4beta,5alpha)-isomer;galgravin, (2alpha,3alpha,4beta,5beta)-(+)-isomer;galgravin, (2alpha,3beta,4alpha,5beta)-isomer;galgravin, (2R-(2alpha,3alpha,4beta,5alpha))-isomer;galgravin, (2S-(2alpha,3beta,4alpha,5beta))-isomer;veraguensin

Chemical Property of Veraguensin

Chemical Property:

• Vapor Pressure: 7.04E-09mmHg at 25°C
• Melting Point: 128.0-129.2℃ (methanol )
• Boiling Point: 479.1°Cat760mmHg
• Flash Point: 190.4°C
• PSA: 46.15000
• Density: 1.082g/cm³
• LogP: 4.80580
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 372.19367399
• Heavy Atom Count: 27
• Complexity: 418

Purity/Quality:

99%, ^*data from raw suppliers

Veraguensin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(OC1C2=CC(=C(C=C2)OC)OC)C3=CC(=C(C=C3)OC)OC)C
• Isomeric SMILES: C[C@H]1[C@@H]([C@H](O[C@H]1C2=CC(=C(C=C2)OC)OC)C3=CC(=C(C=C3)OC)OC)C
• Uses: Veraguensin is a neolignan displaying anti-leishmanial activity against Leishmania amazonensis intracellular amastigotes.

Technology Process of Veraguensin

There total 52 articles about Veraguensin 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: 80.0%

C21H26O5 (1262323-70-5,74683-15-1) + methyl iodide (74-88-4) → veraguensin (528-63-2,10569-12-7,19950-55-1,27686-82-4,50393-84-5,50393-86-7,61949-24-4,81845-14-9,83377-13-3,99882-17-4,102518-40-1,103774-96-5,104112-96-1,104112-97-2,104112-98-3,122872-00-8)

Guidance literature:

With sodium hydride; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2010.10.136

Reference yield: 60.0%

2-chloro-1-(3,4-dimethoxyphenyl)-1-[1-(3,4-dimethoxyphenyl)allyloxy]-2-nitropropane → 2,5-bis(3,4-dimethoxyphenyl)-3,4-dimethyl-3-nitrotetrahydrofuran + (2R*,3R*,4R*,5R*)-2,5-bis(3,4-dimethoxyphenyl)-3,4-dimethyltetrahydrofuran (528-63-2,10569-12-7,19950-55-1,27686-82-4,50393-84-5,50393-86-7,61949-24-4,81845-14-9,83377-13-3,99882-17-4,102518-40-1,103774-96-5,104112-96-1,104112-97-2,104112-98-3,122872-00-8) + (+/-)-ganschisandrin

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 20h; Heating;

DOI:10.1021/ol061666m

Reference yield:

1,4-bis(3,4-dimethoxyphenyl),2,3-dimethylbutane-1,4-dione (4440-92-0) → terameprocol (24150-24-1,927425-26-1) + all-cis-3,4-dimethyl-2,5-bis(3,4-dimethoxyphenyl)tetrahydrofuran (528-63-2,10569-12-7,19950-55-1,27686-82-4,50393-84-5,50393-86-7,61949-24-4,81845-14-9,83377-13-3,99882-17-4,102518-40-1,103774-96-5,104112-96-1,104112-97-2,104112-98-3,122872-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / methanol / 6.5 h / 44 - 54 °C / Inert atmosphere; Large scale

2: palladium 10% on activated carbon; hydrogen / 1-Propyl acetate / 3 h / 100 °C / 51716.2 Torr

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In methanol; 1-Propyl acetate;

DOI:10.1016/j.ejmech.2013.01.028

upstream raw materials:

3,4-dimethyl-2,5-bis(3,4-dimethoxyphenyl)furan

methanol

acetic acid

(2S*,3S*)-1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane-1,4-dione

Downstream raw materials:

2r,5c-Bis-(4,5-dimethoxy-2-nitro-phenyl)-3c,4c-dimethyl-tetrahydro-furan

(+/-)-trans-4-(3,4-dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy-2,3-dimethylnaphthalene

galgravin

(+)-verrucosin

Refernces

• 1、 Jagtap, Pratap R.,Císa?ová, Ivana,Jahn, Ullrich. "Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps". supporting information. p. 750 - 755. Retrieved 2018/02/09.
• 2、 Matcha, Kiran,Ghosh, Subrata. "An asymmetric route to total synthesis of the furano lignan (+)-veraguensin". . p. 6924 - 6927. Retrieved 2011/03/18.