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Kiliani reactions on ketoses: branched carbohydrate building blocks from D-tagatose and D-psicose

Abstract:

D-Tagatose and D-psicose on treatment with sodium cyanide gave mixtures of branched sugar lactones; extraction of the crude products by acetone in the presence of acid permits direct access to branched carbohydrate diacetonides, likely to be of value as new chirons. In both cases, the major lactone products-diacetonides with a 2,3-cis-diol relationship-can be crystallised in around 40-50% yield from the ketohexose. A practical procedure for the conversion of 30 g of D-tagatose to give 24 g of...

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Publication status:
Published

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Authors


Soengas, R More by this author
Izumori, K More by this author
Simone, MI More by this author
Watkin, DJ More by this author
Skytte, UP More by this author
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Journal:
TETRAHEDRON LETTERS
Volume:
46
Issue:
34
Pages:
5755-5759
Publication date:
2005-08-22
DOI:
ISSN:
0040-4039
URN:
uuid:c094a641-3c38-4efc-9e99-ba9b68381913
Source identifiers:
39581
Local pid:
pubs:39581
Language:
English

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