A Three-Pronged Approach to the Global Debenzylation of an Advanced Furanoside Intermediate <i>en Route</i> to Remdesivir

Herein are reported strategies to achieve the global deprotection of an advanced intermediate in the synthesis of remdesivir, the active pharmaceutical ingredient of Veklury and the first antiviral medication approved (October 2020) for the treatment of COVID-19. Three strategies to improve the efficiency of the BCl3-mediated debenzylation reaction were explored: 1) enhanced control over processing conditions via flow chemistry; 2) attenuation of the reactivity of the BCl3 with additive B(OMe)3; and 3) replacement of BCl3/CH2Cl2 with AlCl3/anisole. These three strategies were developed in parallel in pursuit of improved yield and process robustness to expedite the large-scale manufacturing of remdesivir during the COVID-19 outbreak.

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Publication Details

Journal
Organic Process Research & Development
Published
2026-03-15
DOI
https://doi.org/10.1021/acs.oprd.5c00512
Primary Topic
Innovative Microfluidic and Catalytic Techniques Innovation
Type
article
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article

A Three-Pronged Approach to the Global Debenzylation of an Advanced Furanoside Intermediate en Route to Remdesivir

Andrew C. Stevens, Sean Neville, Christopher S. Regens, Nolan D. Griggs et al.
Organic Process Research & Development
Innovative Microfluidic and Catalytic Techniques Innovation
article

A Three-Pronged Approach to the Global Debenzylation of an Advanced Furanoside Intermediate en Route to Remdesivir

Andrew C. Stevens, Sean Neville, Christopher S. Regens, Nolan D. Griggs, Robert R. Milburn, Lina Chan, Todd A. Wenderski, Laura Zilke, Nick Uhlig, Zilin Huang, W. Stacy Bremner, Tiago Vieira, Blanka M. Hodur, Sara A. Bonderoff, B. Michael O’Keefe, Matthew R. Chin, Trevor C. Johnson, Matthew M. Logan
article en

Abstract

Herein are reported strategies to achieve the global deprotection of an advanced intermediate in the synthesis of remdesivir, the active pharmaceutical ingredient of Veklury and the first antiviral medication approved (October 2020) for the treatment of COVID-19. Three strategies to improve the efficiency of the BCl3-mediated debenzylation reaction were explored: 1) enhanced control over processing conditions via flow chemistry; 2) attenuation of the reactivity of the BCl3 with additive B(OMe)3; and 3) replacement of BCl3/CH2Cl2 with AlCl3/anisole. These three strategies were developed in parallel in pursuit of improved yield and process robustness to expedite the large-scale manufacturing of remdesivir during the COVID-19 outbreak.

Organic Process Research & Development
Centre for Process Innovation (GB), Operation PAR (US), Praxis (United States) (US), ClearMotion (United States) (US), Precision for Medicine (United States) (US), Vividion Therapeutics (United States) (US), Gilead Sciences (United States) (US), Gilead Sciences (France) (FR), Global University (LB)
Openalex Percentile: Top 21%
Innovative Microfluidic and Catalytic Techniques Innovation
DOISourceOpenAlex
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