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  4. Asymmetric Synthesis of 2,4,6-Trideoxy-4-(dimethylamino)-3-C-methyl-Llyxohexopyranose (Lemonose)
 
research article

Asymmetric Synthesis of 2,4,6-Trideoxy-4-(dimethylamino)-3-C-methyl-Llyxohexopyranose (Lemonose)

Bernadat, Guillaume
•
George, Nicolas  
•
Couturier, Cedric
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2011
Synlett

L-Lemonose, the glycosidic part of (–)-lemonomycin, has been synthesized in ten steps with 18% overall yield from Dthreonine. The key steps are a double, highly diastereoselective Grignard addition to a Weinreb amide and a chemoselective oxidation of a primary alcohol in the presence of a secondary alcohol, a tertiary alcohol and a tertiary amine, leading directly to the lactol.

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Type
research article
DOI
10.1055/s-0030-1259531
Web of Science ID

WOS:000287575400030

Author(s)
Bernadat, Guillaume
George, Nicolas  
Couturier, Cedric
Masson, Géraldine
Schlama, Thierry
Zhu, Jieping  
Date Issued

2011

Publisher

Georg Thieme Verlag

Published in
Synlett
Issue

4

Start page

576

End page

578

Subjects

sugar

•

aminosugar

•

lemonomycin

•

lemonose tetrahydroisoquinoline

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSPN  
Available on Infoscience
April 4, 2011
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/65918
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