- Synthesis, Photochemistry and Enzymology of 2-O-(2-Nitrobenzyl)-D-glucose, a Photolabile Derivative of D-Glucose
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Alkylation of the dibutylstannylene derivative of methyl 4,6-O-benzylidene-α-D-glucopyranose 2a with 2-nitrobenzyl bromide gave a mixture of 2-O- and 3-O-(2-nitrobenzyl) derivatives 3b and 4 b in the ratio ca.3:1.Chromatographic separation and removal of the protecting groups gave the title compound 1.Regiospecific synthesis by 2-nitrobenzylation of the monoalcohol 8a was examined but could not be achieved efficiently.Compound 1 was neither a substrate for nor an inhibitor of coupled hexokinase/glucose-6-phosphate dehydrogenase enzyme system.On photolysis, it was converted into free glucose with 1:1 stoichiometry.
- Corrie, John E. T.
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p. 2161 - 2166
(2007/10/02)
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- SYNTHETIC STUDIES ON NOGALAMYCIN: STEREOSPECIFIC C-5 ALKYLATION OF A SUGAR DERIVATIVE VIA CLAISEN REARRANGEMENT AND A NEW ROUTE TO 1,1,4-TRIALKOXYBUTA-1,3-DIENES.
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Claisen rearrangement of the 4-methoxybutadienylether of the allylic alcohol 13 which was made in 15 steps from D-glucose, afforded one major aldehyde 17 or 18 in good yield.All attempts to oxidize to an acid were unsuccessful.The model compound 24 and compound 13, were converted respectively to the α, β-unsaturated esters 25 and 26.Compound 25 was further transformed into 1,1,4-trialkoxybuta-1,3-diene 27 which was found unreactive towards quinones.
- Vatele, J.-M.
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p. 4443 - 4450
(2007/10/02)
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