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Hydroxymethyl-Branched Piperidines from Hydroxymethyl-Branched Lactones: Synthesis and Biological Evaluation of 1,5-Dideoxy-2-C-hydroxymethyl-1,5-imino-D-mannitol, 1,5-Dideoxy-2-C-hydroxymethyl-1,5-imino-L-gulitol and 1,5-Dideoxy-2-C-hydroxymethyl-1,5-imino-D-talitol

Abstract:

Three homochiral polyhydroxylated piperidines containing a quaternary carbon branch at C-2 of the heterocyclic ring, which can be considered as branched analogues of deoxymannorijimycin (DMJ), and their corresponding lactams were synthesised from readily available and versatile carbohydrate lactones containing a 2-C-hydroxymethyl branch. The key step in the synthesis of these iminosugars, 1,5-dideoxy-2-C-hydroxymethyl-1,5-imino-D-mannitol, 1,5-dideoxy-2-C-hydroxymethyl-1,5-imino-L-gulitol and...

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Publication status:
Published

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Publisher copy:
10.1002/ejoc.201200054

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Journal:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume:
2012
Issue:
12
Pages:
2394-2402
Publication date:
2012-04-05
DOI:
EISSN:
1099-0690
ISSN:
1434-193X
URN:
uuid:a2018b6c-8669-4c4c-ad0a-ddf7b374b5c6
Source identifiers:
327135
Local pid:
pubs:327135
Language:
English
Keywords:

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