Boc-protected (3R,4S)-3,4-dihydroxypiperidine diol 1 is an enantiomerically pure, highly valuable synthetic intermediate. Herein we report the development of two scalable synthetic strategies avoiding the use of hazardous sodium azide, as well as the formation of azido intermediates. Starting from the readily available 2-deoxy-D-ribose, it was possible to produce a substantial amount of diol 1 following two distinct routes, without a significant decrease in performance when scaling up from 1- to 230-mmol. (c) 2022 Elsevier Ltd. All rights reserved.
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