Comparing the greenness and sustainability of three routes to an HIV protease inhibitor intermediate

Stephanie Gina Akakios, Moira Leanne Bode, Roger Arthur Sheldon

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Abstract

The greenness and sustainability of three different routes for the synthesis of (3R,3aS,6aR)-hexahydrofuro [2,3-b] furan-3-ol (bis-furan alcohol), an advanced intermediate for a group of HIV protease inhibitors, including the FDA approved darunavir, used in antiretroviral (ARV) therapy, were compared. The method involved a comparison of (i) waste generated using theE-factor and relative to industrial benchmarks using the innovative Green Aspiration Level (iGAL™) method, (ii) solvent usage on the basis of solvent intensity (SI) and properties according to the GSK solvent guide, and (iii) Green Motion™ scores according to the MANE methodology.

Original languageEnglish
Pages (from-to)3334-3347
JournalGreen Chemistry
Volume23
Issue number9
DOIs
Publication statusPublished - 2021

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