90633-88-8Relevant academic research and scientific papers
Synthesis of asymmetrically substituted scyllo-inositol
Rodriguez, Jacob,Walczak, Maciej A.
, p. 3281 - 3283 (2016)
scyllo-Inositol, a rare member of the inositol family, is present in axinelloside A, a marine metabolite with interesting inhibitory activity against human telomerase. Here, we present a concise synthesis of asymmetrically substituted scyllo-inositol star
Approaches to Pyranuronic β-Sugar Amino Acid Building Blocks of Peptidosaccharide Foldamers
Goldschmidt G?z, Viktória,Pintér, István,Harmat, Veronika,Perczel, András
, p. 355 - 361 (2018/01/27)
Pyranuronic β-sugar amino acids (β-SAAs) are biocompatible and tuneable building blocks of foldamers and chimera-peptides. The scalable and economical total synthesis of two building blocks is described here. These C-4 epimers, Fmoc-GlcAPU(Me)-OH (7) and
Synthesis and mass spectrometric analysis of disaccharides from methanolysis of heparan sulfate
He, Qi Qi,Trim, Paul J.,Snel, Marten F.,Hopwood, John J.,Ferro, Vito
, p. 8791 - 8803 (2018/11/30)
The quantification of heparan sulfate (HS) in biological matrices, e.g., urine, cerebrospinal fluid, tissue samples etc., is of great importance for the diagnosis and prognosis of several of the mucopolysaccharidosis (MPS) disorders, which are lysosomal storage diseases of impaired glycosaminoglycan metabolism. The development of suitable assays for this purpose is challenging due to the high molecular weight and complexity of HS. Recent efforts towards this goal include the acid catalysed methanolysis of HS, which desulfates the polymer and results in the formation of disaccharide cleavage products which can be detected and quantified by LC-MS/MS. We have synthesized a library of 12 HS-derived disaccharides as methanolysis standards via the stereoselective 1,2-cis glycosylation of suitably protected GlcA and IdoA acceptors with a 2-deoxy-2-azido thioglucoside donor. This facilitated identification of the major peaks in the LC-MS/MS chromatograms, and potentially will allow the monitoring of specific metabolites as surrogate markers for genotype. This work also paves the way towards a fully quantitative LC-MS/MS assay for HS via the preparation of a suitably labelled derivative.
P-chlorobenzyl ether: A p-methoxybenzyl ether in disguise
Viuff, Agnete H.,Heuckendorff, Mads,Jensen, Henrik H.
, p. 5773 - 5775 (2016/11/29)
In the chemistry of polyfunctionalized organic compounds, protecting groups that can undergo mild and selective cleavage while still being stable during the entire synthetic sequence are often required. In this work, we present a straightforward conversion of the robust p-chlorobenzyl ether into the more labile and well-described p-methoxybenzyl ether using palladium catalysis. This reaction was demonstrated to be high yielding and compatible with a wide range of functionalities, thereby providing a useful supplement to the conventional ether protecting groups.
Synthesis of glyco-fused bicyclic compounds; Conformationally constrained scaffolds and useful polyfunctional building blocks
Cardona, Francisco,D'Orazio, Giuseppe,Silva, Artur M. S.,Nicotra, Francesco,La Ferla, Barbara
supporting information, p. 2549 - 2556 (2014/05/06)
We synthesized fused bicyclic polyfunctional compounds containing a highly hydroxylated pyran ring starting from commercially available methyl glucopyranoside and adopting a RCM annulation approach. The versatile α,β-unsaturated ketone group was introduced on the newly formed ring and, as an example of the potential of these polyfunctionalized building blocks, a tetracyclic compound was synthesized through a Diels-Alder cycloaddition reaction. Bicyclic polyfunctional glycol-fused compounds have been synthesized from commercially available methyl gluco-pyranoside. These molecules, with their high chirality content, presence of an α,β-unsaturated ketone and multiple hydroxyl groups represent useful building blocks for the preparation of complex, optically pure compounds. Copyright
Organocatalysis for the acid-free O-arylidenation of carbohydrates
Geng, Yiqun,Faidallah, Hassan M.,Albar, Hassan A.,Mhkalid, Ibrahim A.,Schmidt, Richard R.
supporting information, p. 7035 - 7040 (2013/11/06)
Methyl glycopyranosides of glucose, galactose, and mannose, their 2,3-di-O-benzyl-protected derivatives, as well as the unprotected sugars react with p-methoxybenzaldehyde dimethyl acetal (3) and with benzaldehyde dimethyl acetal (7) as reagents in the presence of thiourea 1 or squaramide 2 as the organocatalyst to afford regioselectively 4,6-O-arylidenated derivatives 5 and 8. With an excess amount of 3 or 7, diarylidenated derivatives are also obtained. In situ formation of acetals of type 3 and 7 from corresponding aldehydes 10 and 13 in the presence of an orthoester and organocatalyst 1 or 2 can be used to generate 5 and 8 directly from the aldehydes. Some substrates also lead to mixed orthoesters with this procedure. The reaction courses are discussed. A squaramide catalyzes the 4,6-O-arylidenation of glucose, mannose, and galactose with the use of arenecarbaldehyde dimethyl acetals or arenecarbaldehydes and orthoesters as the reagents. Glycoside derivatives also undergo this reaction. Copyright
Regioselective Reductive Ring Opening of 4-Methoxybenzylidene Acetals of Hexopyranosides. Access to a Novel Protective Group Strategy
Johansson, Rolf,Samuelsson, Bertil
, p. 201 - 202 (2007/10/02)
Reduction of fully protected 4,6-O-(4-methoxybenzylidene)hexopyranosides with sodium cyanoborohydride-trifluoroacetic acid in N,N-dimethylformamide, or with trimethylsilyl chloride in acetonitrile, gives the 6- and 4-O-(4-methoxybenzyl) ethers, respectively, in good yields and with good regioselectivity; the 4-methoxybenzyl ether linkage in products containing benzyl ethers or other protective groups is selectively cleaved upon treatment with cerium(IV) ammonium nitrate in aqueous acetonitrile.
