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  4. Synthesis of rare carbohydrates and analogues starting from enantiomerically pure 7-oxabicyclo[2.2.1]heptyl derivatives ("naked sugars")
 
research article

Synthesis of rare carbohydrates and analogues starting from enantiomerically pure 7-oxabicyclo[2.2.1]heptyl derivatives ("naked sugars")

Vogel, P.  
2000
Current Organic Chemistry

Recent applications of the "naked sugar" methodology are reviewed. General methods have been developed to transform enantiomerically pure 7-oxabicyclo[2.2.1]heptyl derivatives into rare monosaccharides, carbasugars, into a new doubly-branched imino-dideoxyalditol (iminosugar), into long-chain carbohydrates, C-disaccharides, imino-C-disaccharides and new polyhydroxylated quinolizidines. The methods allow to prepare both enantiomers of a given target with the same ease. Predictable high stereoselectivity of the reactions of the bicyclic chirons adds to the flexibility of the approach that can lead to a large molecular diversity.

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Type
research article
DOI
10.2174/1385272003376175
Author(s)
Vogel, P.  
Date Issued

2000

Published in
Current Organic Chemistry
Volume

4

Issue

5

Start page

455

End page

480

Subjects

Aza-c-disaccharides

•

alpha-glucosidase-i

•

beta-d-xyloside

•

electron

•

donating substituent

•

venous antithrombotic agents

•

chondroitin sulfate

•

chains

•

total asymmetric-synthesis

•

efficient total synthesis

•

ring-expanded analogs

•

diels-alder additions

Note

Univ Lausanne, Chim Sect, BCH, CH-1015 Lausanne, Switzerland.

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LGSA  
Available on Infoscience
November 9, 2005
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/219772
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