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ChemicalBook CAS DataBase List Anidulafungin
166663-25-8

Anidulafungin synthesis

4synthesis methods
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

    • 202112070005324267.jpg

    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.

  • ROUTE 2

    • 202112070324686589.jpg

    Wei, Changyong; Liu, Jian; Ma, Yaping; Yuan, Jiancheng. Process for preparation of anidulafungin. Assignee Hybio Pharmaceutical Co., Ltd. 2013.

  • ROUTE 3

    • 202112075612439130.jpg

    Grutsch, John Leo, Jr.; Hansen, Marvin Martin; Harkness, Allen Robert; Udodong, Uko Effiong; Verral, Daniel Edward, II. Phosphonylation agents for synthesis of cyclic peptide antifungal agents. Assignee Eli Lilly and Company. 1999.

  • ROUTE 4

    • 202112075764356779.jpg

    Alaparthi, Lakshmi Prasad; Mantri, Anand Vijaykumar; Kumar, Huchanna Yogish; Bhushaiah, Chowdary Talluri; Kulkarni, Gaurav; Ramu, Vasanthakumar Ganga. Intermediates and processes to prepare anidulafungin. 2016.

  • ROUTE 5

    • 202112073176302006.jpg

    Subramanian, Venkatesan Chidambaram; Sathiyanarayanan, Singaram; Raju, Siva Pota Linga; Reddy, Nidra Venka. 2-[[[4''-(Pentyloxy)-1,1':4',1''-terphenyl-4-yl]carbonyl]oxy]-4,6-dimethoxy-1,3,5-triazine intermediate in a process for the preparation of anidulafungin. Assignee Gland Pharma Ltd. 2017.

202112070005324267.jpg

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.

-

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]

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