ChemicalBook CAS DataBase List Anidulafungin

Anidulafungin synthesis

4synthesis methods

Product Name:Anidulafungin
CAS Number:166663-25-8
Molecular formula:C58H73N7O17
Molecular Weight:1140.24

Anidulafungin, also known as LY303366, is a semisynthetic echinocandin used as an antifungal drug. Anidulafungin was approved on 2/21/2006. Anidulafungin has proven efficacy against esophageal candidiasis, but its main use will probably be in invasive Candida infection; it may also have application in treating invasive Aspergillus infection. It is a member of the class of antifungal drugs known as the echinocandins; its mechanism of action is by inhibition of (1→3)-β-D-glucan synthase, an enzyme important to the synthesis of the fungal cell wall. Anidulafungin inhibits glucan synthase, an enzyme important in the formation of (1→3)-β-D-glucan, a major fungal cell wall component. Glucan synthase is not present in mammalian cells, so it is an attractive target for antifungal activity.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

Norris, Timothy; VanAlsten, John; Hubbs, Stephen; Ewing, Marcus; Cai, Weiling; Jorgensen, Matthew L.; Bordner, Jon; Jensen, Grace O. Commercialization and Late-Stage Development of a Semisynthetic Antifungal API: Anidulafungin/D-Fructose (Eraxis). Organic Process Research & Development. Volume 12. Issue 3. Pages 447-455. 2008.

619-44-3
302 suppliers
$6.00/10g

166663-25-8
276 suppliers
$28.00/1mg

Yield:-

Steps:

Multi-step reaction with 4 steps
1: 1.) sec-butyllithium, 2.) triisopropyl borate, 3.) K₂CO₃, tetrakis(triphenylphosphine)palladium⁽⁰⁾
2: 2 N aq. NaOH / dioxane / 17 h / Heating
3: dicyclohexylcarbodiimide / CH₂Cl₂ / Ambient temperature
4: dimethylformamide / Ambient temperature

References:

Debono, Manuel;Turner, William W.;LaGrandeur, Lisa;Burkhadt, Fred J.;Nissen , Jeffrey S.;et al. [Journal of Medicinal Chemistry,1995,vol. 38,# 17,p. 3271 - 3281]

63619-51-2 Synthesis

63619-51-2
29 suppliers
$9.00/250mg

166663-25-8
276 suppliers
$28.00/1mg

References

[1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-

158938-08-0
96 suppliers
$15.00/250mg

166663-25-8
276 suppliers
$28.00/1mg

References

4''-(Pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxylic acid methyl ester

158937-30-5
7 suppliers
inquiry

166663-25-8
276 suppliers
$28.00/1mg

References

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