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Preliminary studies on the transformation of nitrosugars into branched chain iminosugars: synthesis of 1,4-dideoxy-4-C-hydroxymethyl-1,4-imino-pentanols.

Abstract:

A novel promising strategy for the transformation of nitrosugars into branched pyrrolidines, based on double Henry reaction with formaldehyde followed by reductive ring closure, allowed the first enantiospecific synthesis of a 4-C-hydroxymethyl branched derivative of the well-known glycosidase inhibitor 1,4-dideoxy-1,4-imino-pentanol. This strategy also afforded a new route to some other interesting derivatives, such as N-hydroxy, N-propyloxy, and imino derivatives, a new kind of compounds wi...

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Publication status:
Published

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Publisher copy:
10.1021/ol062887v

Authors


Soengas, RG More by this author
Estévez, JC More by this author
Estévez, RJ More by this author
Watkin, DJ More by this author
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Journal:
Organic letters
Volume:
9
Issue:
4
Pages:
623-626
Publication date:
2007-02-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:8dd89985-441f-42b5-9801-7ad33e67bbb6
Source identifiers:
33751
Local pid:
pubs:33751

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