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2-Nitrobenzyl glycosides

Scheme 3.—Proposed Mechanism for the Photochemical Cleavage of 2-Nitrobenzyl Ethers and 2-Nitrobenzyl Glycosides. Scheme 3.—Proposed Mechanism for the Photochemical Cleavage of 2-Nitrobenzyl Ethers and 2-Nitrobenzyl Glycosides.
Photolytic deprotection of the ulosonic acid -nitrobenzyl glycoside (49) did not yield the expected enolpyranose but the rearranged 3-dehydroquinic acid (50) the stereospecific label rearrangement implies a chair transition state, and suggests the biosynthetic pathway by this route is not enzyme-catalysed. ... [Pg.187]

Flavone C-glycosides Pure compounds FAB (+) m-nitrobenzyl alcohol Glycerol 282... [Pg.86]

The application of diazo coupling is somewhat limited by the availability of the p-aminophenyl glycosides, particularly of those of the oligosaccharides. Their precursors, the p-nitrophenyl glycosides, are usually obtained by the condensation of a per-O-acetylated glycosyl halide with p-nitrophenol in ethanol (Michael reaction)19,20 or by the reaction of a per-O-acetylated sugar with p-nitrophenol in the presence of a Lewis acid catalyst (Helferich reaction).21 p-Nitrobenzyl 1-thioglycosides have also been prepared by the condensation of the... [Pg.230]

SCHEME.—Syntheses of allyl glycosides of distal disaccharide units of GPLs from M. avium serovars 4 and 20 involving regioselective substitutions in the preparations of glycosyl acceptors. MPM = 4-methoxyphenylmethyl [p-methoxybenzyl] NPM = 2-nitrophenylmethyl [o-nitrobenzyl]. [Pg.214]

Zehavi, U., Amit, B. and Patchornik, A. (1972) light-sensitive glycosides. I. 6-Nitroveratryl p-D-glucopyranoside and 2-nitrobenzyl p-D-glucopyranoside. Journal of Organic Chemistry 37, 2281—2285. [Pg.440]

Example of light-sensitive glycosides 2-nitrobenzyl and 6-nitroveratryl glycosides... [Pg.158]

Polystyrene incorporating an o-nitrobenzyl alcohol group (insoluble) Polymer-saccharide glycoside. Photolysis of polymer O-nitro-benzyl glycoside at 320 nm Isomaltose Zehavi and Patchomik, 1973... [Pg.109]

Sialic acids have also been coupled to proteins. To investigate the haptenic properties of sialic acid, the p-nitrobenzyl a-glycoside of N-acetylneuraminic acid... [Pg.71]

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2-nitrobenzyl

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