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6R-, and 6S, -6C-methylglucose from D-glucuronolactone: Efficient synthesis of a seven carbon fucose analogue: Inhibition of some enzymes of primary metabolism

Abstract:

Syntheses of the two epimeric 6C-methylglucoses from D-glucuronolactone rely on a non-stereoselective reduction of an intermediate lactol. A highly stereoselective reduction of a silylated lactol, which is accompanied by a silyl migration, gives easy access to 6S-6C-methylglucose - a seven carbon fucose analogue - in five steps from glucuronolactone in an overall yield of 40%. An azido analogue of 6R-6C-methylglucose is also reported, Such compounds may provide new materials for the selective...

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Publication status:
Published

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Journal:
TETRAHEDRON More from this journal
Volume:
53
Issue:
44
Pages:
15135-15146
Publication date:
1997-11-03
DOI:
ISSN:
0040-4020
Language:
English
Pubs id:
pubs:45766
UUID:
uuid:8a1649b9-51bc-4841-aa25-6a144b9fd75b
Local pid:
pubs:45766
Source identifiers:
45766
Deposit date:
2012-12-19

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