87326-73-6Relevant articles and documents
A chemoselective oxidation of monosubstituted ethylene glycol: Facile synthesis of optically active α-hydroxy acids
Chinthapally, Kiran,Baskaran, Sundarababu
, p. 4305 - 4309 (2014/06/23)
A mild and efficient method for the synthesis of optically active α-hydroxy acids through chemoselective oxidation of monosubstituted ethylene glycols using the TEMPO-NaOCl reagent system is described. It is evident from our studies that the solvent, pH and reaction temperature are very crucial for the success of this oxidation. The versatility of this method has been demonstrated with a variety of aliphatic, aromatic and carbohydrate substrates bearing various functional groups. the Partner Organisations 2014.
PROCESS FOR PREPARATION OF FONDAPARINUX AND ITS INTERMEDIATES
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, (2013/03/26)
The present invention relates to a process for the preparation of 3-O-benzyl- 1,2-O- isopropylidene-α-D-glucofuranuronic acid (Formula IV) and ester (Formula V) thereof. The process comprises benzylation of l,2:5,6-di-O-isopropylidene-α-D-glucofuranose (Formula I; hereinafter, referred to as diacetone-D-glucose) in the presence of tetrabutylammonium bromide, followed by selective hydrolysis of the product formed (Formula II) using sulfuric acid to obtain 3-O-benzyl- 1,2-O-isopropylidene-α-D- glucofuranose (Formula III). Compound of Formula III is then oxidized to compound of Formula IV which upon esterification provides corresponding ester of Formula V. The process of the invention can be used in the production of fondaparinux sodium, a heparin and blood clotting factor Xa inhibitor.(Formula I, II, III, IV, V) (I) (II) (III) (IV) (V) wherein R is optionally branched alkyl group.
Toward the assembly of heparin and heparan sulfate oligosaccharide libraries: efficient synthesis of uronic acid and disaccharide building blocks
Saito, Akihiro,Wakao, Masahiro,Deguchi, Hiroshi,Mawatari, Aya,Sobel, Michael,Suda, Yasuo
experimental part, p. 3951 - 3962 (2010/07/04)
The monosaccharide moieties found in heparin (HP) and heparan sulfate (HS), glucosamine and two kinds of uronic acids, glucuronic and iduronic acids, were efficiently synthesized by use of glucosamine hydrochloride and glucurono-6,3-lactone as starting compounds. In the synthesis of the disaccharide building block, the key issues of preparation of uronic acids (glucuronic acid and iduronic acid moieties) were achieved in 12 steps and 15 steps, respectively, without cumbersome C-6 oxidation. The resulting monosaccharide moieties were utilized to the syntheses of HP/HS disaccharide building blocks possessing glucosamine-glucuronic acid (GlcN-GlcA) or iduronic acid (GlcN-IdoA) sequences. The disaccharide building blocks were also suitable for further modification such as glycosylation, selective deprotection, and sulfation.