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Periodate oxidation products of some partially methylated hexoses and hexitols

University of British Columbia

Chairman: Professor G.G.S. Dutton Periodate Oxidation Products of Some Partially Methylated Hexoses and Hexitols Complete periodate oxidation of 2,3-di-O-methyl-D-glucitol and 2,3-di-O-methyl-D-mannitol produced 2,3-di-O-methyl-L-threose and 2,3-di-0-methyl-D-erythrose respectively. Reduction with sodium borohydride produced the corresponding tetritols, 2,3-di-O-methyl-L-threitol and 2,3-di-0-methyl-erythritol. Incomplete periodate oxidation of the two hexitols lead to the formation of large amounts of the respective pentoses, 3,4-di-0-methyl-L-xylose and 3,4-di-O-methyl-D-arabinose. Attempts to prepare 4-0-methyl-D-threose from methyl 6-0-methyl-αβ-D-galactofuranoside and 2-0-methyl-D-erythrose from methyl 4-0-methyl-α-D-mannopyranoside by periodate oxidation were only partially successful. Although the oxidation proceeded smoothly, the cleavage of the oxidized product could not be readily effected with mineral acid, methanolysis or mercaptolysis without extensive degradation taking place. Reduction of the aldehydes generated by periodate oxidation allowed the facile preparation of the corresponding tetritols. A scheme to correlate the original aldehyde structure to the reduced tetritol is proposed. The structure of an unknown component in the hydrolysis of methyl 2,3-di-0-methyl-α-D-glucopyranoside in the presence of 2,3-di-0-methyl-D-glucitol was shown to be 1,4-anhydro-2,3-di-0-methyl-D-glucitol. The paper chromatographic characteristics of the prepared tetroses, tetritols and pentoses in the two most commonly used solvent systems have been recorded.

Text

2011-08-03

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http://hdl.handle.net/2429/36480

Chemistry

University of British Columbia

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