Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars.

Org Biomol Chem

Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. and National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, PR China.

Published: May 2016

Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-d-mannitol) was the acetonation of d-mannose.

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http://dx.doi.org/10.1039/c6ob00531dDOI Listing

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Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars.

Org Biomol Chem

May 2016

Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. and National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, PR China.

Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-d-mannitol) was the acetonation of d-mannose.

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