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6R- and 6S-6C-Methylmannose from D-mannuronolactone. Inhibition of phosphoglucomutase and phosphomannomutase: agents for the study of the primary metabolism of mannose

Abstract:

The syntheses of 6S-3 and 6R-6 6C-methylmannoses rely on opposite and highly stereoselective reductions of fully and partially protected ketones derived from D-mannuronolactone, respectively. Reduction of the silylated ketone 2 by sodium borohydride was accompanied by complete migration of the silyl protecting group to the new stereogenic centre; the silyl migration was suppressed when the reduction was conducted in the presence of cerium(III) chloride. Both epimers were good inhibitors of ph...

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Publication status:
Published

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Journal:
TETRAHEDRON-ASYMMETRY
Volume:
10
Issue:
2
Pages:
355-366
Publication date:
1999-01-29
DOI:
ISSN:
0957-4166
Language:
English
Pubs id:
pubs:36951
UUID:
uuid:89753fb9-0236-47ce-b2c6-89c06a312dd3
Local pid:
pubs:36951
Source identifiers:
36951
Deposit date:
2012-12-19

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