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Kiliani on ketoses: branched carbohydrate building blocks from D-fructose and L-sorbose

Abstract:

Protected branched sugar lactones are available via Kiliani-acetonation sequences on readily available ketoses such as d-fructose and l-sorbose. In both cases, the readily crystallized diacetonides have a 2,3-cis-diol relationship in the product lactone. An efficient double inversion of the configuration at C-4 and C-5 of the product from d-fructose gives access to the formal Kiliani product from l-psicose. Branched carbohydrate lactones are likely to be of significant value as chirons for ho...

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Publication status:
Published

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Authors


Hotchkiss, D More by this author
Soengas, R More by this author
Simone, MI More by this author
van Ameijde, J More by this author
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Journal:
TETRAHEDRON LETTERS
Volume:
45
Issue:
51
Pages:
9461-9464
Publication date:
2004-12-13
DOI:
ISSN:
0040-4039
URN:
uuid:22bf03c1-dc7a-45ec-8e1a-ed120a6d206e
Source identifiers:
39286
Local pid:
pubs:39286
Language:
English

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