182298-38-0Relevant academic research and scientific papers
Scalable synthesis of L-lduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides
Hansen, Steen Uldall,Barath, Marek,Salameh, Bader A.B.,Pritchard, Robin G.,Stimpson, William T.,Gardiner, John M.,Jayson, Gordon C.
supporting information; experimental part, p. 4528 - 4531 (2009/12/09)
L-ldo cyanohydrln 3 was prepared from dlacetone-D-glucose In four steps and 76% overall yield and 90% de via cyanohydrin reaction of aldehyde 2. This process can be scaled to provide >1 mol of pure L-Ido cyanohydrin 3. Cyanohydrin 3 was elaborated to 1,2-Isopropylldineprotected L-ldo nitrile (8), lduronic amide 9, and known carboxy ester 10. Coupling of 8 and 9 with glucosamine donors leads to new types (6-cyano and 6-carboxamlde) of heparin-related disaccharides.
PRODUCTION OF L-IDURONATE CONTAINING POLYSACCHARIDES
-
Page/Page column 47; 49; 50; 61; 62; 63, (2008/06/13)
The present invention provides processes for the production of polysaccharides containing the L-iduronate subunit, for example, heparin-type polysaccharides. New intermediate compounds and processes developed during the production of said polysaccharides are also presented.
Stereospecific addition of formaldehyde dialkylhydrazones to sugar aldehydes. Synthesis of cyanohydrins and α-hydroxy aldehydes
Lassaletta, Jose M.,Fernandez, Rosario,Martin-Zamora, Eloisa,Pareja, Carmen
, p. 5787 - 5790 (2007/10/03)
Formaldehyde dialkylhydrazones smoothly add to sugar aldehydes without any need of promoter or catalyst. α-Hydroxy dialkylhydrazones, which are obtained in good yields and high stereoselectivities, have been successfully transformed in cyanohydrins by treatment with magnesium monoperoxyphtalate (MMPP) and in O-protected α-hydroxy aldehydes by ozonolysis or HCl mediated hydrolysis. No racemization was observed in the cleavage of the dialkylhydrazone group.
