Part 1. 2-Deoxy-C-glycofuranosides from D-glucose. Part 2. An approach to N-acetylneuraminic acid from carbohydrate precursors.

Persistent Link:
http://hdl.handle.net/10150/186329
Title:
Part 1. 2-Deoxy-C-glycofuranosides from D-glucose. Part 2. An approach to N-acetylneuraminic acid from carbohydrate precursors.
Author:
Wijayaratne, Thusitha Udayangani.
Issue Date:
1993
Publisher:
The University of Arizona.
Rights:
Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
Abstract:
Part 1: 4,6-0-Benzylidene methyl glucoside undergoes periodic oxidation resulting in a sesqui-acetal which may be regarded as a protected erythrose. The use of the Wittig reaction on this protected erythrose and similar derivatives to extend the number of carbons by one was studied. Ring closure under oxymercuration conditions should lead to C-l substituted 2- deoxyfuranosides. This short, convergent approach to C-glycofuranosides can be extended to C-nucleoside synthesis if the preparation of an appropriate heterocyclic Wittig reagent can be achieved. Part 2: N-Acetylneuraminic acid, a 9-carbon sugar, is the most abundant member in the sialic acid family. Retrosynthetic analysis shows C-3, C-4 bond disconnection is logical. This synthetic strategy involves: 1. Synthesis of the fully protected mannosamine derivative: fully protected glucosamine was synthesized. 2. Stereoselective C3-C4 bond formation: model reactions were carried out and the desired threo β-amino alcohol was the major isomer in the product mixture. 3. Conversion of the 3-carbon nucleophile to an α keto ester or α keto acid: We have explored different oxidative conditions on model compounds.
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Dissertations, Academic.; Chemistry, Organic.
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Chemistry; Graduate College
Degree Grantor:
University of Arizona
Committee Chair:
Polt, Robin L.

Full metadata record

DC FieldValue Language
dc.language.isoenen_US
dc.titlePart 1. 2-Deoxy-C-glycofuranosides from D-glucose. Part 2. An approach to N-acetylneuraminic acid from carbohydrate precursors.en_US
dc.creatorWijayaratne, Thusitha Udayangani.en_US
dc.contributor.authorWijayaratne, Thusitha Udayangani.en_US
dc.date.issued1993en_US
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en_US
dc.description.abstractPart 1: 4,6-0-Benzylidene methyl glucoside undergoes periodic oxidation resulting in a sesqui-acetal which may be regarded as a protected erythrose. The use of the Wittig reaction on this protected erythrose and similar derivatives to extend the number of carbons by one was studied. Ring closure under oxymercuration conditions should lead to C-l substituted 2- deoxyfuranosides. This short, convergent approach to C-glycofuranosides can be extended to C-nucleoside synthesis if the preparation of an appropriate heterocyclic Wittig reagent can be achieved. Part 2: N-Acetylneuraminic acid, a 9-carbon sugar, is the most abundant member in the sialic acid family. Retrosynthetic analysis shows C-3, C-4 bond disconnection is logical. This synthetic strategy involves: 1. Synthesis of the fully protected mannosamine derivative: fully protected glucosamine was synthesized. 2. Stereoselective C3-C4 bond formation: model reactions were carried out and the desired threo β-amino alcohol was the major isomer in the product mixture. 3. Conversion of the 3-carbon nucleophile to an α keto ester or α keto acid: We have explored different oxidative conditions on model compounds.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectDissertations, Academic.en_US
dc.subjectChemistry, Organic.en_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.chairPolt, Robin L.en_US
dc.contributor.committeememberBates, Robert B.en_US
dc.contributor.committeememberGervay, Jacquelynen_US
dc.contributor.committeememberWigley, David E.en_US
dc.contributor.committeememberWalker, F. Annen_US
dc.identifier.proquest9333333en_US
dc.identifier.oclc720045346en_US
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