research article

Synthesis of 4-hydroxy-2,6-bis(hydroxymethyl)tetrahydropyran-2-carbaldehyde derivatives

Turner, D.
•
Vogel, P.  
1998
Synlett

Cycloaddition of 1,3-dibromo-2-oxyallyl cation to 2-(benzyloxymethyl)furan provided a 8-oxabicyclo[3.2.1]hept-6-en-3-one derivative that was transformed into (2RS,3SR,4SR,5SR,6SR)-3,4-dibromo-2-benzyloxymethyl-2,6-bis(hydroxymethy l)-4- (methoxymethyloxy)tetrahydropyran. Selective protection and oxidation produced a protected 3,5-dibromo-4-hydroxy-2,6-bis(hydroxymethyl)tetrahydropyran-2-carbaldehy de that could be used to carry out cross-aldolisations, opening an approach to the synthesis of C-disaccharide analogues mimicking sialic acid glycosides.

Cite this item

Turner, D., & Vogel, P. (1998). Synthesis of 4-hydroxy-2,6-bis(hydroxymethyl)tetrahydropyran-2-carbaldehyde derivatives. Synlett, (3), 304–306. https://doi.org/10.1055/s-1998-1629

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Type
research article
DOI
10.1055/s-1998-1629
Author(s)
Turner, D.
Vogel, P.  
Date Issued

1998

Published in
Synlett
Issue

3

Start page

304

End page

306

Subjects

Chemical-enzymatic synthesis

•

n-acetylneuraminic acid

•

sialyl-lewis-x

•

aldol condensation

•

c-glycosides

•

selectin

•

ketones

•

inhibitors

•

cations

Note

Univ Lausanne, BCH Dorigny, Chim Sect, 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/20.500.14299/219740