Conformationally armed glycosyl donors: reactivity quantification, new donors and one pot reactions

2008 ◽  
pp. 2465 ◽  
Author(s):  
Christian Marcus Pedersen ◽  
Lavinia G. Marinescu ◽  
Mikael Bols
Keyword(s):  
One Pot ◽  
New Donors ◽  
Glycosyl Donors

Substoichiometric FeCl3 Activation of Propargyl Glycosides for the Synthesis of Disaccharides and Glycoconjugates

Synlett ◽  
2018 ◽  
Vol 29 (05) ◽  
pp. 668-672 ◽  
Author(s):  
Jianbo Zhang ◽  
Guosheng Sun ◽  
Yue Wu ◽  
Anqi Liu ◽  
Saifeng Qiu ◽  
...  
Keyword(s):  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Optimal Reaction ◽  
Glycosyl Donors

Glycosides as glycosyl donors using FeCl3 have been described. Under optimal reaction conditions, three kinds of propargyl glycosides were found to react with steroids and sugar-derived glycosyl acceptors to afford the corresponding disaccharides and glycoconjugates in good to excellent yields (66–91%). Meanwhile, the method can also realize one-pot synthesis of disaccharides, making it an effective, affordable, and green glycosylation procedure.

scholarly journals Benzyne arylation of oxathiane glycosyl donors

2010 ◽  
Vol 6 ◽  
Author(s):  
Martin A Fascione ◽  
W Bruce Turnbull
Keyword(s):  
Lead Tetraacetate ◽  
One Pot ◽  
Glycosyl Donors

The arylation of bicyclic oxathiane glycosyl donors has been achieved using benzyne generated in situ from 1-aminobenzotriazole (1-ABT) and lead tetraacetate. Following sulfur arylation, glycosylation of acetate ions proceeded with high levels of stereoselectivity to afford α-glycosyl acetates in a ‘one-pot’ reaction, even in the presence of alternative acceptor alcohols.

Efficient one-pot synthesis of 2-hydroxyethyl per-O-acetyl glycosides

2014 ◽  
Vol 68 (8) ◽  
Author(s):  
Hong-Wen Tao ◽  
Xia Wang ◽  
Ping-Gui Yi ◽  
Zhi-Hong Deng ◽  
Xian-Yong Yu ◽  
...  
Keyword(s):  
Hydrogen Fluoride ◽  
Trans Configuration ◽  
Experimental Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Acetyl Group ◽  
Glycosyl Donors

AbstractA class of stereo-isomerically-pure alkanediol monoglycosides, 2-hydroxyethyl per-O-acetyl pyranosides (IIIa-IIIf), was conveniently prepared by a one-pot reaction of per-O-acetylated pyranoses (Ia-If) and 2-(tert-butyldimethylsilyloxy)ethanol (II) with catalysis by BF3·OEt2. The α-(IIIa) or β-linked glycosides (IIIb-IIIf) with 1,2-trans-configuration were obtained from glycosyl donors with participation of the neighbouring 2-O-acetyl group. BF3·OEt2, along with hydrogen fluoride released from BF3·OEt2 under the experimental conditions used, facilitates the subsequent de-protection of siloxane to successfully afford 2-hydroxyethyl per-O-acetyl-pyranosides.

A strategy for the one-pot synthesis of sialylated oligosaccharides

2002 ◽  
Vol 80 (8) ◽  
pp. 1051-1054 ◽  
Author(s):  
Zhiyuan Zhang ◽  
Kenichi Niikura ◽  
Xue-Fei Huang ◽  
Chi-Huey Wong
Keyword(s):  
Sialic Acid ◽  
One Pot ◽  
One Pot Synthesis ◽  
New Strategy ◽  
The One ◽  
Glycosyl Donors

A new strategy has been developed for the synthesis of branched sialylated oligosaccharides using one-pot technology. Sialyl donors are in general too weak in reactivity to be used as the first glycosyl donors in the one-pot synthesis. When sialic acid is linked to a different sugar such as galactose, the reactivity is, however, significantly enhanced and can be tuned to enable the one-pot synthesis. A combination of NIS–TfOH–AgOTf was used for activation of the thioglycosides to improve the glycosylation yield when a hindered acceptor was used, as illustrated in the one-pot assembly of sialylated hexasaccharide.Key words: one-pot synthesis, sialyl oligosaccharides, new activation.

scholarly journals Conformationally superarmed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot

2017 ◽  
Vol 15 (3) ◽  
pp. 559-563 ◽  
Author(s):  
Mithila D. Bandara ◽  
Jagodige P. Yasomanee ◽  
Nigam P. Rath ◽  
Christian M. Pedersen ◽  
Mikael Bols ◽  
...  
Keyword(s):  
Building Blocks ◽  
Oligosaccharide Synthesis ◽  
One Pot ◽  
Glycosyl Donors

A new series of superarmed glycosyl donors has been investigated.

β-Selective One-Pot Synthesis of Acyl-C-Glycosides via Corey–Seebach Umpolung Reaction

Synlett ◽  
2019 ◽  
Vol 30 (17) ◽  
pp. 1935-1939
Author(s):  
G. Jacob Boehlich ◽  
Nina Schützenmeister
Keyword(s):  
Drug Development ◽  
One Pot ◽  
One Pot Synthesis ◽  
Selective Approach ◽  
Chemical Hydrolysis ◽  
Glycosyl Donors

C-Glycosides are commonly used as carbohydrate mimics in drug development due to their stability against enzymatic and chemical hydrolysis. In this Synpacts article we elaborate on our fast and efficient β-selective approach towards protected and unprotected acyl glycosides. Application of a Corey–Seebach umpolung reaction enables the exclusive formation of the β-anomer of aromatic acyl-C-glycosides in good to excellent yields.1 Introduction2 C-Glycosylation of Benzylated Glycosyl Donors3 C-Glycosylation of Silylated Glycosyl Donors4 Conclusion

scholarly journals Synthesis of the tetrasaccharide repeating unit of the O-specific polysaccharide of Azospirillum doebereinerae type strain GSF71T using linear and one-pot iterative glycosylations

2020 ◽  
Vol 16 ◽  
pp. 1700-1705
Author(s):  
Arin Gucchait ◽  
Pradip Shit ◽  
Anup Kumar Misra
Keyword(s):  
Perchloric Acid ◽  
Good Yield ◽  
Type Strain ◽  
One Pot ◽  
Synthetic Strategy ◽  
Specific Polysaccharide ◽  
Glycosyl Donors

A straightforward synthetic strategy was developed for the synthesis of the tetrasaccharide repeating unit corresponding to the O-specific polysaccharide of Azospirillum doebereinerae type strain GSF71T in a very good yield adopting sequential glycosylation followed by removal of the p-methoxybenzyl (PMB) group in the same pot. Further, the synthetic strategy was modified by carrying out three stereoselective iterative glycosylations followed by in situ removal of the PMB group in one pot. The stereochemical outcome of the newly formed glycosidic linkages was excellent using thioglycoside derivatives as glycosyl donors and a combination of N-iodosuccinimide (NIS) and perchloric acid supported on silica (HClO4-SiO2) as the glycosyl activator.

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