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Volumn 73, Issue 16, 2008, Pages 6437-6440

Microwave-enhanced ionothermal CuAAC for the synthesis of glycoclusters on a calix[4]arene platform

Author keywords

[No Author keywords available]

Indexed keywords

CALIX[4]ARENE; CHEMICAL EQUATIONS; ETHYNYL; GLYCOCLUSTERS;

EID: 50149098979     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800954z     Document Type: Article
Times cited : (73)

References (63)
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    • Synthesis in an ionic liquid is known as ionothermal synthesis to distinguish it from hydrothermal preparations, which take place in water and other molecular solvents, see: Cooper, E. R, Andrews, C. D, Wheatley, P. S, Webb, P. B, Wormald, P, Morris, R. E. Nature 2004, 430, 1012-1016
    • Synthesis in an ionic liquid is known as ionothermal synthesis to distinguish it from hydrothermal preparations, which take place in water and other molecular solvents, see: Cooper, E. R.; Andrews, C. D.; Wheatley, P. S.; Webb, P. B.; Wormald, P.; Morris, R. E. Nature 2004, 430, 1012-1016.
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    • Experiments run in a single-mode cavity dedicated reactor Biotage Initiator. Temperature measured externally on the outside vessel wall by an IR sensor.
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    • 13C NMR analysis as described in our recent publications. See refs 13, 17e, g and: (a) Cheshev, P.; Dondoni, A.; Marra, A. Org. Biomol. Chem. 2006, 4, 3225-3227.
    • 13C NMR analysis as described in our recent publications. See refs 13, 17e, g and: (a) Cheshev, P.; Dondoni, A.; Marra, A. Org. Biomol. Chem. 2006, 4, 3225-3227.
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    • For the isolation and X-ray structure determination of such intermediate from a model click reaction, see: (a) Nolte, C, Mayer, P, Straub, B. F. Angew. Chem, Int. Ed. 2007, 46, 2101-2103
    • For the isolation and X-ray structure determination of such intermediate from a model click reaction, see: (a) Nolte, C.; Mayer, P.; Straub, B. F. Angew. Chem., Int. Ed. 2007, 46, 2101-2103.
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    • The same mechanism cannot operate by using calix[4]arene alkynes. Accordingly we observed that a sluggish reaction takes place between an upper rim tetra-ethynyl-calix[4]arene and a C-glycosylmethyl azide see ref 17e
    • The same mechanism cannot operate by using calix[4]arene alkynes. Accordingly we observed that a sluggish reaction takes place between an upper rim tetra-ethynyl-calix[4]arene and a C-glycosylmethyl azide (see ref 17e).
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    • A referee suggested that more than a single copper atom is involved in the reaction, i.e, dinuclear alkynyl copper(I) complexes, as reported in recent papers, see ref 21 and (a) Ahlquist, M, Fokin, V. V. Organometallics 2007, 26, 4389-4391
    • A referee suggested that more than a single copper atom is involved in the reaction, i.e., dinuclear alkynyl copper(I) complexes, as reported in recent papers, see ref 21 and (a) Ahlquist, M.; Fokin, V. V. Organometallics 2007, 26, 4389-4391.
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    • The glycocluster 9 was transformed into the free hydroxy sugar derivative 9-OH (see Supporting Information).
    • The glycocluster 9 was transformed into the free hydroxy sugar derivative 9-OH (see Supporting Information).
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    • A tris-sialoside was isolated in 13% yield as previously observed when the reaction of 2 and 8 was carried out in DMF. See ref 17g
    • A tris-sialoside was isolated in 13% yield as previously observed when the reaction of 2 and 8 was carried out in DMF. See ref 17g.
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    • We found that the cycloaddition in IL 4 at 80°C between a C-glucosyl acetylene and a 6-azido-glucoside described in our previous work (ref 13) required 16 h under thermal heating and only 2 h using MW dielectric heating.
    • We found that the cycloaddition in IL 4 at 80°C between a C-glucosyl acetylene and a 6-azido-glucoside described in our previous work (ref 13) required 16 h under thermal heating and only 2 h using MW dielectric heating.


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