13299-05-3

Upstream product

• 150-76-5 4-methoxy-phenol 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 62446-93-9 1,2,3,4-tetra-O-acetyl-D-xylopyranose 
• 106820-14-8 2,3,4-Tri-O-acetyl-D-xylopyranose 
• 128376-91-0 2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate 
• 87-72-9 D-Xylose 

Downstream Products

• 475101-58-7 4-methoxyphenyl 2,3-O-isopropylidene β-D-xylopyranoside 
• 475101-59-8 4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->4)-β-D-xylopyranoside 
• 475101-60-1 4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside 
• 721438-51-3 4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside 
• 475101-62-3 4-methoxyphenyl O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside 
• 475101-61-2 4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside 
• 1350309-51-1 4-methoxyphenyl 2-O-acetyl-3,6-di-O-benzyl-4-O-triisopropylsilyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-α-D-xylopyranoside 
• 1350309-50-0 4-methoxyphenyl 2,4-di-O-acetyl-3,6-di-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-α-D-xylopyranoside 

Relevant academic research and scientific papers

Total Synthesis of Pseudomonas aeruginosa 1244 Pilin Glycan via de Novo Synthesis of Pseudaminic Acid

Pseudaminic acid (Pse) is a nonulosonic acid unique to bacterial species, found as a component of important cell surface glycans and glycoproteins in various pathogenic species, such as the critical hospital threat Pseudomonas aeruginosa. Herein we present the development of a facile and scalable de novo synthesis of Pse and its functionalized derivatives from easily available Cbz-l-allo-threonine methyl ester (16 steps in 11% yield). The key reactions in our de novo synthesis involve the diastereoselective glycine thioester isonitrile-based aldol-type reaction to create the 1,3-anti-diamino skeleton, followed by the Fukuyama reduction and the indium-mediated Barbier-type allylation. Moreover, we have studied the glycosylation of the Pse glycosyl donors and identified the structural determinants for its glycosylation diastereoselectivity, which enabled us to complete the total synthesis of P. aeruginosa 1244 pilin trisaccharide α-5NβOHC47NFmPse-(2→4)-β-Xyl-(1→3)-FucNAc.

The application of aryl substituted derivatives of xylose as environmentally friendly multipurpose pesticides

A series of aryl substituted derivatives of xylose have been synthesized. Biological tests have revealed high fungicidal activity of the resulting compounds against various phythopathogenic fungi. Additional biological studies have demonstrated high plant growth regulatory activity of the compounds synthesized.

Synthetic study and structural analysis of the antifreeze agent xylomannan from Upis ceramboides

The novel antifreeze factor, xylomannan, first isolated from the freeze-tolerant Alaskan beetle Upis ceramboides, demonstrates a high degree of thermal hysteresis, comparable to that of the most active insect antifreeze proteins. Although the presence of a lipid component in this factor has not yet been verified, it has been proposed that the glycan backbone consists of a β-d-mannopyranosyl-(1→4)-β-d-xylopyranose-disaccharide-repeating structure according to MS and NMR analyses. In this contribution, we report the stereoselective synthesis of the tetrasaccharide β-d-mannopyranosyl- (1→4)-β-d-xylopyranosyl-(1→4)-β-d-mannopyranosyl-(1→4) -d-xylopyranoside, a structural component of xylomannan. Our synthesis features the use of 2-naphthylmethyl (NAP)-ether-mediated intramolecular aglycon delivery (IAD) as the key reaction in obtaining β-mannopyranoside stereoselectively. Various donors for NAP-IAD were tested to determine the most suitable for the purposes of this synthesis. Fragment coupling between a disaccharyl fluoride and a disaccharide acceptor obtained from a common β-d-mannopyranosyl-(1→4)-β-d-xylopyranoside derivative was successfully carried out to afford the desired tetrasaccharide in the presence of Cp2HfCl2-AgClO4. Structural analysis of the resulting synthetic tetrasaccharide using NMR techniques and molecular modeling was performed in order to demonstrate the presence of the proposed xylomannan linkages in this molecule.

Lanthanum trifluoromethane-sulfonate-catalyzed facile synthesis of per-O-acetylated sugars and their one-pot conversion to S-aryl and O-alkyl/aryl glycosides

Lanthanum trifluoromethanesulfonate-catalyzed solvent-free per-O-acetylation with stoichiometric acetic anhydride proceeds in high yield (95%-99%) to afford exclusively pyranose products as anomeric mixtures. Subsequent anomeric substitution employing borontrifluoride etherate and thiols or alcohols furnished the corresponding 1,2-trans-linked thioglycosides and O-glycosides, respectively, in good to excellent overall yield (75%-85%). Alternatively, reaction of free sugars in neat alcohol employing the same catalyst at elevated temperature gives the corresponding 1,2-cis-linked O-glycosides (along with 1,2-trans-linked glycosides as minor product) in good yield (73%-80%). Anomeric mixtures of compounds thus produced were characterized as their per-O-acetylated derivatives.

Synthetic approach toward the partial sequences of betaglycan in the linkage region on solid support and in solution phase

We have synthesized, for the first time, the partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer. Stepwise elongation afforded the corresponding tetraosyl trichloro

Synthesis of betaglycan-type tetraosyl hexapeptide: a possible precursor regulating enzymatic elongation toward heparin.

TETRAOSYL HEXAPEPTIDE, A PART OF THE SEQUENCE OF BETAGLYCAN: beta-D-GlcA-(1-->3)-beta-D-Gal-(1-->3)-beta-D-Gal-(1-->4)-beta-D-Xyl-(1-->O-SerGlyTrpProAspGly (1), which was designed as a probe for glycan elongation toward heparin, was synthesized in a stere

Enzymatic β-galactosidation of modified monosaccharides: Study of the enzyme selectivity for the acceptor and its application to the synthesis of disaccharides

The selectivity of the E. coli β-galactosidase-catalyzed glycosylation of monosaccharides differently substituted at the anomeric position has been studied. Substituents bearing a phenyl ring increase the enzyme-acceptor binding; however, partial enzyme inhibition occurs. The regioselectivity of the glycosylation was dependent on small variations in the monosaccharide acceptor, such as the atom linked to the anomeric carbon and the number of methylenes between this atom and aromatic ring. A schematic model is proposed that accounts for the results. The information from this study allows the direct synthesis of disaccharides, with high regioselectivity and yields ranging from 30 to 40%.