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  4. Total Asymmetric-Synthesis of 5-Deoxy-5-Thio-L-Allose
 
research article

Total Asymmetric-Synthesis of 5-Deoxy-5-Thio-L-Allose

Emery, F.
•
Vogel, P.  
1994
Journal of Carbohydrate Chemistry

The optically pure Diels-Alder adduct of furan to 1-cyanovinyl (1R)-camphanate was converted to methyl(methyl 5-bromo-5-deoxy-2,3-O-isopropylidene-beta-L-allo-hexo-furanosid)uronate. Ester reduction, followed by HBr elimination afforded (+)-methyl 5,6-anhydro-2,3-O-isopropylidene-D-beta-talo-hexofuranoside. Applying the method of Adley and Owen, (+)-methyl 5,6-dideoxy-5,6-epithio-2,3-O-isopropylidene-L-beta-allo-hexofuranoside was obtained and acetolysed to give, after deprotection, (-)-5-deoxy-5-thio-L-allose.

  • Details
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Type
research article
DOI
10.1080/07328309408011664
Author(s)
Emery, F.
Vogel, P.  
Date Issued

1994

Published in
Journal of Carbohydrate Chemistry
Volume

13

Issue

4

Start page

555

End page

563

Subjects

Derivatives naked sugars

•

5-thiopyranoses

•

triacetate

•

arabinose

•

furan

•

acid

Note

Univ lausanne,chim sect,ch-1005 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/20.500.14299/219689
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