Armed–disarmed effect of remote protecting groups on the glycosylation reaction of 2,3-dideoxyglycosyl donors

Tomono, Satoshi; Kusumi, Shunichi; Takahashi, Daisuke; Toshima, Kazunobu

doi:10.1016/j.tetlet.2011.02.109

Cited by 8 publications

(4 citation statements)

References 30 publications

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“…Remote participation of certain protecting groups to facilitate the glycosidic bond formation with 2‐deoxy thioglycosides has also been studied . Mong and co‐workers have shown the effects of picoloyl (Pico) group, illustrating their role for the glycosylation with deoxy glycoside donors.…”

Section: Glycosylationsmentioning

confidence: 99%

Chemical O‐Glycosylations: An Overview

2016

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The development of glycobiology relies on the sources of particular oligosaccharides in their purest forms. As the isolation of the oligosaccharide structures from natural sources is not a reliable option for providing samples with homogeneity, chemical means become pertinent. The growing demand for diverse oligosaccharide structures has prompted the advancement of chemical strategies to stitch sugar molecules with precise stereo‐ and regioselectivity through the formation of glycosidic bonds. This Review will focus on the key developments towards chemical O‐glycosylations in the current century. Synthesis of novel glycosyl donors and acceptors and their unique activation for successful glycosylation are discussed. This Review concludes with a summary of recent developments and comments on future prospects.

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Section: Glycosylationsmentioning

confidence: 99%

Chemical O‐Glycosylations: An Overview

2016

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“…Subsequent acidic hydrolysis of the acetonide and acetylation furnished 3,4-di-O-acetyl-GalNTCAc donor 20. To exploit the arming effect of an ether protecting group, [17,18] we also examined the synthesis of a 4-O-benzyl-GalNTCAc donor. In this case, triol 15 was converted into 6-OH derivative 23 via 4,6-benzylidenation [19] , acetylation, and reductive ring cleavage of the benzylidene group using TESH and PhBCl 2 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of ganglioside analogs containing fluorescently labeled GalNAc for single-molecule imaging

Koikeda

Komura

Tanaka

et al. 2019

Journal of Carbohydrate Chemistry

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Gangliosides, glycosphingolipids containing sialic acid(s) in the glycan moieties, as major constituents of functional membrane domains such as lipid rafts participate in various biological processes. Previously, we developed fluorescent ganglioside analogs useful for single-molecule imaging of lipid raft formations. In this paper, we describe the development of a, 6-N 3 -GalNTCAc donor and its application to the synthesis of fluorescent gangliosides containing fluorescent GalNAc residue(s) at the glycan terminus, namely, fluorescent analogs of GalNAc-GD1a and asialo-GM2.

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“…In another recent study, the armed-disarmed effect of remote protecting groups at C4 and/or C6 on the glycosylations of the 2,3-dideoxyglycosyl acetates, which possess different protecting groups at C4 and C6, with a glycosylacceptor 2 was investigated by Toshima et al 22 the armed-disarmed effect of the remote protecting groups. Moreover, it should be noted that the stereoselectivity of the disaccharides 50 and 51 was found to be reversed from a to b probably because of the participation effect of the Bz group at C4 (Scheme 38.13).…”

Section: Direct Synthetic Methodsmentioning

confidence: 99%