1999
DOI: 10.1021/ja982232s
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Abstract: In an effort to develop a broadly applicable approach to the facile one-pot synthesis of oligosaccharides, the reactivity of a number of p-methylphenyl thioglycoside (STol) donors which are either fully protected or have one hydroxyl group exposed has been quantitatively determined by HPLC. We have characterized and quantified the influence on reactivity of the structural effects of different monosaccharide cores and different protecting groups on each glycoside donor. In addition, we have established a correl… Show more

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Cited by 839 publications
(726 citation statements)
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References 53 publications
(39 reference statements)
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“…Both species were found to be more energetically favoured than the non-coordinated oxocarbenium ion. Optimizing experiments were first conducted with common activating conditions, such as NIS/AgOTf, NIS/TMSOTf and Ph 2 SO/Tf 2 O/TTBP ( In general, the structure of glycosyl acceptors only shows complementary effects 28 on stereoselectivity of a glycosylation reaction, compared with the structure of donors [29][30][31] , and other factors such as temperature or solvents. Glycosyl acceptors bearing electron-withdrawing substituents should diminish the nucleophilicity of the hydroxyl group, resulting in a decrease of reaction rate 29,32 .…”
Section: Resultsmentioning
confidence: 99%
“…Both species were found to be more energetically favoured than the non-coordinated oxocarbenium ion. Optimizing experiments were first conducted with common activating conditions, such as NIS/AgOTf, NIS/TMSOTf and Ph 2 SO/Tf 2 O/TTBP ( In general, the structure of glycosyl acceptors only shows complementary effects 28 on stereoselectivity of a glycosylation reaction, compared with the structure of donors [29][30][31] , and other factors such as temperature or solvents. Glycosyl acceptors bearing electron-withdrawing substituents should diminish the nucleophilicity of the hydroxyl group, resulting in a decrease of reaction rate 29,32 .…”
Section: Resultsmentioning
confidence: 99%
“…The results of growth regulation activity tests given in Figures 1-3 show that synthetic pentasaccharide and heptasaccharide promote the growth of maize plants and also stimulate the growth of roots. After supplementing with oligosaccharides for a week, pentasaccharide increased the mass of plants by 21.4%, while heptasaccharide increased the mass of plants by 10.7%. When supplemented with oligosaccharides for 3 weeks, pentasaccharide improved by 23.6%, and heptasaccharide improved by 32.7%.…”
Section: Resultsmentioning
confidence: 97%
“…8 The Troc group also gives higher β-selectivities than other groups. 9 Also, the Troc group as an N-protecting group enhances glucosamine-4-hydroxy-acceptor reactivity when compared to other Nprotecting groups, 10 and can be removed under mild conditions.…”
Section: Resultsmentioning
confidence: 99%