A New Method for the Synthesis of 2,3-Aziridino-2,3-dideoxyhexonamides and Their Conversion into 3-Amoni-2,3-dideoxyhexonic Acids.

Christel Thea Jørgensen, Christian Pedersen, Inger Søtofte

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

The new 2,3-Aziridino-2,3-dideoxyhexonamides 3 and 11 were prepared by a three-step procedure from commercially available D-glucono-1,5-lactone and D-gulono-1,4-lactone, respectively. The lactones were converted into methyl 3,4;5,6-di-O-isopropylidene-2-Omesyl esters 2 and 10, which upon treatment with ammonia formed the title aziridino compounds. These were reductively cleaved by hydrazine to give 3-amino-2,3-dideoxyhexonic hydrazides 13 and 15, which were easily converted into corresponding lactone 14 and acid 16, respectively.
Original languageEnglish
JournalSynthesis
Volume1998
Issue number3
Pages (from-to)325-328
ISSN0039-7881
Publication statusPublished - 1998

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