139437-39-1Relevant articles and documents
N-O bond as a glycosidic-bond surrogate: Synthetic studies toward polyhydroxylated N-alkoxypiperidines
Malik, Ga?lle,Ferry, Angélique,Guinchard, Xavier,Cresteil, Thierry,Crich, David
supporting information, p. 2168 - 2179 (2013/03/29)
A series of novel polyhydroxylated N-alkoxypiperidines has been synthesized by ring-closing double reductive amination (DRA) of highly functionalized 1,5-dialdehydes with various hydroxylamines. The required saccharide-based dialdehydes were prepared efficiently from sodium cyclopentadienylide in seven steps. A two-step protocol has been developed for the DRA; it led, after deprotection, to isofagomine, 3-deoxyisofagomine, and numerous other N-alkoxy analogues. The barrier to inversion in these polyhydroxylated N-alkoxypiperidine derivatives was found by variable-temperature NMR methods to be approximately 15 kcal mol-1. With the exception of N-hydroxyisofagomine itself, none of the compounds prepared showed significant inhibitory activity against sweet almond β-glucosidase. Copyright
Structure and stereochemistry of an anti-inflammatory anhydrosugar from the Australian marine sponge Plakinastrella clathrata and the synthesis of two analogues
Katavic, Peter L.,Yong, Ken W.L.,Herring, Joel N.,Deseo, Myrna A.,Blanchfield, Joanne T.,Ferro, Vito,Garson, Mary J.
, p. 8074 - 8079 (2013/08/23)
The structure and relative/absolute configuration of the C-15:0 iso-branched fatty acyl 1,6-anhydropyranose 1 isolated from the Australian marine sponge Plakinastrella clathrata have been investigated. Synthesis of the C-16:0 side chain-modified analogues
EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM
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Page/Page column 27, (2012/05/20)
The present invention relates to a process for the synthesis of the Factor Xa anticoagulent Fondaparinux and related compounds. The invention relates, in addition, to efficient and scalable processes for the synthesis of various intermediates useful in the synthesis of Fondaparinux and related compounds.