Direct glycosylation with anomeric hydroxy sugars by activation with 3-fluorophthalic anhydride and trifluoromethanesulfonic anhydride

Baek, Ju Yuel; Lee, Bo Young; Pal, Rita; Lee, Won Yong; Kim, Kwan Soo

doi:10.1016/j.tetlet.2010.09.064

Cited by 14 publications

(11 citation statements)

References 33 publications

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“…The title compound was obtained from donor 14 and acceptor 22 by typical glycosylation method in 13% yield (α-only) with no HOFox and 98% yield (α-only) with 25 mol % of HOFox as white amorphous solid. The analytical data for the title compound was in accordance to that reported previously …”

Section: Experimental Sectionsupporting

confidence: 87%

“…Thus, glycosidation of donor 14 with 2-OH acceptor 20 34 to form disaccharide 21 was enhanced from 27% (no HOFox) to 85% (25 mol % HOFox, entry 2). Both reactions were stopped after 3 h. Glycosidation of donor 14 with 3-OH acceptor 22 34 to form disaccharide 23 41 was enhanced from 13% (6 h, no HOFox) to 98% (2 h, 25 mol % HOFox, entry 3). Glycosidation of donor 14 with 4-OH acceptor 24 34 to form disaccharide 25 18 was enhanced from 14% (3 h, no HOFox) to 86% (3 h, 25 mol % HOFox, entry 4).…”

Section: Resultsmentioning

confidence: 99%

“…The analytical data for the title compound was in accordance to that reported previously. 41 Methyl 2,3,6-Tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzoyl-α-Dmannopyranosyl)-α-D-glucopyranoside (25). The title compound was obtained from donor 14 and acceptor 24 by typical glycosylation method in 14% yield (α-only) with no HOFox and 86% yield (α-only) with 25 mol % of HOFox as a white amorphous solid.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Regenerative Glycosylation

et al. 2017

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Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.

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Section: Experimental Sectionsupporting

confidence: 87%

Section: Resultsmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Regenerative Glycosylation

et al. 2017

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“…However, gradual decrease of product yield was observed as the reaction scale increased. When we changed phthalic anhydride to 3-fluorophthalic anhydride, we obtained slightly better results up to 245 mg scale, but not at larger scale. On the other hand, coupling reaction with t -butylphthalic anhydride produced the desired disaccharide 9 in 68–75% yield independent to the scale of anomeric hydroxy sugar 8 .…”

mentioning

confidence: 81%

Phthalic Anhydride-Mediated Direct Glycosylation of Anomeric Hydroxy Arabinofuranose: Synthesis of Repeating Oligoarabinofuranoside and Tetradecasaccharide Arabinan Motif of Mycobacterial Cell Wall

Lee

Baek

et al. 2016

J. Org. Chem.

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An efficient direct phthalic anhydride-mediated one-pot glycosylation method employing anomeric hydroxy arabinofuranose as glycosyl donor and triflic anhydride as activating agent has been developed. This method afforded the desired di- and oligoarabinofuranosides in good yields even in gram scale glycosylation when t-butylphthalic anhydride was used. Moreover, our new method can be further extended to the syntheses of repeating oligoarabinofuranoside and tetradecasaccharide arabinan motif found in mycobacterial cell wall.

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“…Glycosyl donor 8 was synthesized according to literature [39] . Acceptors used for the obtainment of the reported glycosides are commercially available, except for compounds 29 and 30 that were synthesized according to literature [40] …”

Section: Methodsmentioning

confidence: 99%

Solvent‐Free Glycosylation from per‐O‐Acylated Donors Catalyzed by Methanesulfonic Acid

et al. 2021

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The huge importance of carbohydrates and their derivatives in biomedical and industrial applications call for the development of streamlined and sustainable procedures for their synthetic elaboration. Here reported a novel glycosylation method based on direct activation of readily available per‐O‐acylated (acetylated or benzoylated) donors, promoted under air by methanesulfonic acid as a cheap and green catalyst in the absence of any solvent. Besides the beneficial avoidance of toxic and polluting organic solvents, these conditions were found critical for activating such poorly reactive donors with a very small catalyst loading (only 5 mol %), instead of stoichiometric Lewis acid promoters typically employed. Desired glycosides were quickly obtained, in most cases with high 1,2‐transstereoselectivity. Other main advantages over reported glycosylations with similar donors are the limited stoichiometric excess of the acceptor (or the donor), the easy applicability and low cost of the procedure and the wide target scope, also covering the synthesis of disaccharides and other non‐trivial glycosides with applicable potential.

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Direct glycosylation with anomeric hydroxy sugars by activation with 3-fluorophthalic anhydride and trifluoromethanesulfonic anhydride

Cited by 14 publications

References 33 publications

Regenerative Glycosylation

Regenerative Glycosylation

Phthalic Anhydride-Mediated Direct Glycosylation of Anomeric Hydroxy Arabinofuranose: Synthesis of Repeating Oligoarabinofuranoside and Tetradecasaccharide Arabinan Motif of Mycobacterial Cell Wall

Solvent‐Free Glycosylation from per‐O‐Acylated Donors Catalyzed by Methanesulfonic Acid

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