Concise Synthesis of 1,4-Dideoxy-1,4-imino-l-arabinitol (LAB) from d-Xylose by Intramolecular Stereospecific Substitution of a Hydroxy Group

Author:

Akkarasamiyo Sunisa1,Sakonnakhon Hatairat Promsaka Na1,Kuntiyong Punlop2,Ploypradith Poonsakdi34,Samec Joseph S. M.5

Affiliation:

1. Department of Chemistry, Special Research Unit for Advanced Magnetic Resonance (AMR), Faculty of Science, Kasetsart University

2. Department of Chemistry, Faculty of Science, Silpakorn University, Sanamchandra Palace Campus

3. Laboratory of Medicinal Chemistry, Chulabhorn Research Institute

4. Program in Chemical Biology, Chulabhorn Graduate Institute, Chulabhorn Royal Academy

5. Department of Organic Chemistry, Stockholm University

Abstract

AbstractWe report a concise and green total synthesis of 1,4-dideoxy-1,4-imino-l-arabinitol hydrochloride from naturally occurring d-xylose. The key step involves a stereospecific substitution of a hydroxy group, without prior derivatization, in which the only byproduct is water. This opens up a novel benign route to iminosugar derivatives with diverse biological activities.

Funder

Kasetsart University Research and Development Institute

Kasetsart University Pre-Proposal Research Fund

Kasetsart University Undergraduate Research Matching Fund

Swedish Research Council FORMAS

Swedish Research Council VETENSKAPSRÅDET

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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