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UBC Theses and Dissertations
Periodate oxidation products of some partially methylated hexoses and hexitols Gibney, Kelly Blair
Abstract
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.
Item Metadata
Title |
Periodate oxidation products of some partially methylated hexoses and hexitols
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Creator | |
Publisher |
University of British Columbia
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Date Issued |
1967
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Description |
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.
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Language |
eng
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Date Available |
2011-08-03
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Provider |
Vancouver : University of British Columbia Library
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Rights |
For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.
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DOI |
10.14288/1.0062253
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Degree Grantor |
University of British Columbia
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Campus | |
Scholarly Level |
Graduate
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Aggregated Source Repository |
DSpace
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For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.