33208-47-8Relevant academic research and scientific papers
AN EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM
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Page/Page column 15, (2013/08/15)
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.
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
Synthesis and glycosidase inhibitory activity of noeurostegine - A new and potent inhibitor of β-glucoside hydrolases
Rasmussen, Tina Secher,Jensen, Henrik Helligso
supporting information; experimental part, p. 433 - 441 (2010/02/16)
A new, stable hemi-aminal nor-tropane christened noeurostegine was synthesised in 22 steps from levoglucosan and tested for inhibitory activity against glycoside hydrolases. Sweet almond and Thermotoga maritimaβ- glucosidases, coffee bean α-galactosidase,
Total synthesis of n-acetylglucosamine-1,6-anhydro-n- acetylmuramylpentapeptide and evaluation of its turnover by ampd from escherichia coli
Hesek, Dusan,Lee, Mijoon,Zhang, Weilie,Noll, Bruce C.,Mobashery, Shahriar
supporting information; experimental part, p. 5187 - 5193 (2009/09/30)
The bacterial cell wall is recycled extensively during the course of cell growth. The first recycling event involves the catalytic action of thelytic transglycosylase enzymes, which produce an uncommon 1,6-anhydropy ranose moiety during separation of the muramyl residues from the peptidoglycan, the major constituent of the cell wall. This product, an N-acetyl-β-D-glucosamine- (1→4)-1,6-anhydro-N-acetyl-β-Dmuramylpeptide, is either internalized to initiate the recycling process or diffuses into the milieu to cause stimulation of the pro-inflammatory responses by the host. We report the total syntheses of N-acetyl-β-Dglucosamine-( 1→4)-1,6-anhydro-N-acetyl- β-D-muramyl-L-Ala-γ-D-Glu-meso-DAP-D-Ala-D-Ala (compound 1, the product of lytic transglycosylase action on the cell wall of Gram-negative bacteria) and N-acetyl-β-Dglucosamine-( 1→4)-1,6-anhydro-N-acetyl- β-D-muramyl-L-Ala-γ-D-Glu-L-Lys-D-Ala-D-Ala (compound 2, from lytic transglycosylase action on the cell wall of Gram-positive bacteria). The syntheses were accomplished in 15 linear steps. Compound 1 is shown to be a substrate of the AmpD enzyme of the Gram-negative bacterium Escherichia coli, anenzyme that removes the peptide from the disaccharide scaffold in the e arly cytoplasmic phase of cell wall turnover.
A facile synthesis of Cerny epoxides and selectively blocked derivatives of 2-azido-2-deoxy-β-D-glucopyranose
Xue, Jie,Guo, Zhongwu
, p. 6487 - 6489 (2007/10/03)
1,6:2,3-Dianhydro-β-D-glucopyranose and its 3-alkylated derivatives were prepared from D-glucal in one pot with overall isolated yields of 60-70%, and these Cerny epoxides were further conveniently converted to selectively blocked 2-azido-2-deoxy-β-D-glucopyranose derivatives by azido opening of the epoxide ring.
Synthesis of 1,6-Anhydro-2-chloro-2,3,4-trideoxy-β-D-erythro-hex-3-enopyranose and its Stereospecific SN2' Substitution
Matsumoto, Masakatsu,Ishikawa, Hiromi,Soya, Yoshihiro,Ozawa, Takayuki
, p. 2377 - 2382 (2007/10/02)
The chlorination of 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose (2) with SOCl2 and pyridine gives predominantly 1,6-anhydro-2-chloro-β-D-erythro-hex-3-enopyranose (3).The chloride (3) takes place exclusively the suprafacial SN2' substit
PREPARATION OF 2-AMINO-1,6-ANHYDRO-2-DEOXY-β-D-MANNOPYRANOSE BY INTRAMOLECULAR SUBSTITUTION OF THE TOSYLOXY GROUP IN STERICALLY HINDERED POSITION OF 1,6-ANHYDRO-2-O-p-TOLYLSULFONYL-β-D-GLUCOPYRANOSE
Cerny, Miloslav,Vecerkova, Hana,Cerny, Ivan,Pacak, Josef
, p. 1837 - 1844 (2007/10/02)
1,6:3,4-Dianhydro-2-O-p-tolylsulfonyl-β-D-galactopyranose (I) was converted to 1,6-anhydro-4-O-benzyl-2-O-p-tolylsulfonyl-β-D-glucopyranose (II) and then reacted with benzylisocyanate to give 3-O-(N-benzylcarbamoyl) derivative III.The cyclization of this
