Yukishige Ito

A simple procedure and compatibility with a variety of manipulations encountered in oligosaccharide synthesis–these advantages are features of this stereoselective synthesis of β-mannosides. The acetal 2 was obtained smoothly from the protected fluoride 1. Subsequent activation of the anomeric position afforded β-mannoside stereoselectively in good yields. CH2X = p-methoxybenzyl.

Methodology toward the stereoselective 1,2-cis glycoside linkage using intramolecular aglycon delivery (IAD) has been extensively developed. In the last two decades, progress has been made using various mixed acetal linkages and a number of glycosyl donor moieties to develop novel IAD strategies, mainly based on formation of acetal linkages. This account summarizes the newest naphthylmethyl (NAP) ether-mediated IAD as well as all the types of mediations for stereospecific construction of various

A novel use of polymer supported glycosyl donor for stereoselective synthesis of β-manno glycoside is described. This system features the use of polymer support in an unprecedented manner, in which the polymer sector serves as a “gatekeeper”. Polymer supported thiomannoside 10 that carries a p-alkoxybenzyl group as a linker at C-2 position was synthesized. This compound was subjected to the conditions of β-mannosylation according to the procedure of p-methoxybenzyl assisted intramolecular aglyco

Only a single purification step is required to isolate the glycoconjugate-related oligosaccharides prepared by a new strategy, which is shown schematically below. Prior to purification the support-bound oligosaccharide, which is labeled with a hydrophobic tag, is cleaved from the polymeric support and deprotected.

Highly efficient and stereoselective β-mannosylation was achieved by using mannosyl thioglycosides 5 and 19. Intramolecular aglycon delivery (IAD) from mixed acetal 12, 15 and 20, obtainable by oxidative coupling of aglycon onto mannosyl thio-glycosides which carry p-methoxybenzyl (PMB) group at C-2 position, was performed by the action of MeOSO2CF3 to afford β-mannosides 13/16/21. It is to be noted that efficiency of IAD was substantially improved by changing the protecting group at the 4- and

Abstract A methodology directed towards the stereoselective construction of 1,2‐ cis ‐glycosides through naphthylmethyl (NAP) ether mediated intramolecular aglycon derivery (IAD) has been developed. Stereospecific constructions of various 1,2‐ cis linkages, as in β‐mannopyrano‐, β‐arabinofurano‐, and α‐glucopyranosides, were achieved through NAP‐IAD. This methodology was successfully applied to the synthesis of Glcα(1→2)‐Glcα(1→3)‐Glcα(1→3)Man (Glc 3 Man 1 ), the nonreducing terminal structure o

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthetic studies on cell-surface glycans. 65. Highly stereoselective synthesis of ganglioside GD3Yukishige Ito, Masaaki Numata, Mamoru Sugimoto, and Tomoya OgawaCite this: J. Am. Chem. Soc. 1989, 111, 22, 8508–8510Publication Date (Print):October 1, 1989Publication History Published online1 May 2002Published inissue 1 October 1989https://doi.org/10.1021/ja00204a028RIGHTS & PERMISSIONSArticle Views449Altmetric-Citations85LEARN ABOUT THESE METRICSArticl

Quality control: UDP-glucose:glycoprotein glucosyltransferase (UGGT) works as the folding sensor in glycoprotein quality control. It glucosylates the Man9GlcNAc2 of misfolded glycoproteins to produce Glc1Man9GlcNAc2, which is a ligand of calnexin and calreticulin. The synthetic substrate Man9GlcNAc2-MTX can be used for the quantitative analysis of UGGT. UDP=uridine 5′-diphosphate, Glc=D-glucose, Man=D-mannose, GlcNAc=N-acetyl-D-glucosamine, MTX=methotrexate.