Sugar amine with various sugars

In our early work, we attempted the alkylation of the amine 81 with various carbohydrate triflates, namely 82-84 [57]. Somewhat disappointingly, the main products isolated were the alkenes, e.g. 85 and 86. Only a small amount of the desired N-linked carbasugar, e. g. 87 was ever obtained. At one stage we attempted an alkylation of the amine 81 with the triflate 82 and with the triflate 84 in the presence of potassium carbonate to our surprise, carbamates were formed, 88 and 89 These two carbamates have subsequently been deprotected to give the methyl -o-glucoside 90 and the free sugar 91, interesting candidates for enzyme inhibition studies [57]. 

Ogura and Takahashi18,19 detailed the reaction of the sugar isothiocyanates 2, 30, 31, and 32 with ammonia and amines, as well as with various classes of hydrazines. The reaction of sugar isothiocyanates with various classes of amines,44"62 hydrazines,63 72 and hydrazides has been reported by... 

In a series of publications and patents,63 64 66"79 Wieniawski and coworkers reported the results of investigations of the reaction of sugar isothiocyanates with amines and various substituted hydrazides of heterocyclic acids. The reaction of isothiocyanate 2 with 2,6-diaminopyridine 81 was described,63 and the formation of dithioureide 82 as the sole product was observed. The... 

Mixtures of various sugars with amines were refluxed in ethanol for 10 min. The reddish-brown mixtures were developed on silica gel TLC plates and sprayed with 2,4-dinitrophenylhydra-zine (2,4-DNP). As shown in Fig. 9, a particular spot at around Rf 0.7 was observed immediately after the spraying in every case, and an additional spot was also detected in the cases of ti-butylamine and cyclohexylamine. These spots agreed well in Rf... 

Formation of novel free radical products at an early stage of the Maillard reaction was demonstrated by use of ESR spectrometry. Analyses of the hyperfine structures for various sugar-amino compound systems led to the conclusion that the radical products are N,N -disubstituted pyrazine cation radicals. These new pyrazine derivatives are assumed to be formed by bimolecular condensation of a two-carbon enaminol compound involving the amino reactant residue. The presence of such a two-carbon product in an early stage reaction mixture of sugar with amine was demonstrated by isolation and identification of glyoxal dialkylimine by use of TLC, GLC, NMR, MS and IR. 

The interaction between nitro sugars and a number of aliphatic, cycloaliphatic, and aromatic amines has been found to proceed, in principle, in the way described for ammonia, although gradual differences, connected with various basicities and, presumably, steric requirements of the amines, are observed. Sowden and associates147 studied the addition of each of seven amines to the tetraacetate of... 

Amino sugars obtained by reductive amination with alkylamine instead of ammonia have various applications. l-Deoxy-l-methylamino-o-glucitol, for instance, is used as hydrophilic component, in particular to obtain water-soluble salts of... 

Later, Shaw and co-workers further employed sugar derived aldehydes 312 as electrophiles in the chalcogeno-MBH reaction (Scheme 2.170). The resulting allyl chlorides 313 can be easily transformed into allylamines 314 via treatment with various amine (Et2NH, pyrrolidine, piperidine and piperazine derivatives) (Scheme 2.170). They also evaluated these allyl chlorides and allylamines for their biological activity and found that (Z)-keto allyl chlorides possess antimycobacterial activity. ... 

Condensation reactions. These are based on the reaction of glucose in hot acetic acid with various aromatic amines, e.g. aniline or o-toluidine to produce coloured derivatives. Other sugars can also react, giving falsely high values. 

Various V-substituted 6-amino-6-deoxy-D-glucose derivatives, e.g. 6-8, were synthesized by reaction of the corresponding 5,6-anhydro-D-glucose derivative with secondary amines, and shown to be useful as non-ionic surfactants capable of forming reverse micelles for solubilization of amino acids in hexane. Reaction of such tertiary amines with methyl iodide provided quaternary ammonium-sugar derivatives. The 6-amino-2,5-anhydro-6-deoxy-D-gluconate derivative 10, a potential dipeptide isostere, was obtained from the C2-symmetric, D-mannitol derived bis-epoxide 9 following silica-assisted azidolysis (Scheme 3). Its enantiomer was obtained similarly from an L-iditol bis-epoxide. ... 

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