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Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology

By Sagandira, Cloudius R.; Watts, Paul

Published on CMKC

Abstract

Tamiflu is one of the most effective anti-influenza drugs, which is currently manufactured by Hoffmann-La Roche from shikimic acid. Owing to its importance, more than 60 synthetic routes have been developed to date, however, most of the synthetic routes utilise the potentially hazardous azide chemistry making them not green, thus not amenable to easy scale up. Consequently, this study exclusively demonstrated safe and efficient handling of potentially explosive azide chemistry involved in a proposed Tamiflu route by taking advantage of the continuous-flow technology. The azide intermediates were safely synthesised in full conversions and >89% isolated yields.

Journal

Beilstein Journal of Organic Chemistry. Volume 15, 2019, 2577–2589

DOI

10.3762/bjoc.15.251

Type of publication

Peer-reviewed journal

Affiliations

  • Nelson Mandela University

Article Classification

Research Article

Classification Areas

  • Intermediate

Tags