1. Anionic additions to glycosyl iodides 2. Neutral addition of alcohols to glycosyl iodides 3. Glycosyl iodides in solid phase oligosaccharide synthesis

Persistent Link:
http://hdl.handle.net/10150/282665
Title:
1. Anionic additions to glycosyl iodides 2. Neutral addition of alcohols to glycosyl iodides 3. Glycosyl iodides in solid phase oligosaccharide synthesis
Author:
Hadd, Michael Joseph
Issue Date:
1998
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:
The usefulness of glycosyl iodides in carbohydrate chemistry has been demonstrated. Both anionic and neutral nucleophiles have been shown to react readily with glycosyl iodides as the glycosyl donor. High yields and stereoselectivity were obtained along with short reaction times. Anionic nucleophiles gave β glycosides selectively, whereas neutral nucleophiles gave α glycosides in the presence of tetrabutylammonium iodide. Initial investigation of the applicability of these glycosidation conditions to solid phase oligosaccharide synthesis has been accomplished.
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Chemistry, Organic.
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Graduate College; Chemistry
Degree Grantor:
University of Arizona
Advisor:
Gervay, Jacquelyn

Full metadata record

DC FieldValue Language
dc.language.isoen_USen_US
dc.title1. Anionic additions to glycosyl iodides 2. Neutral addition of alcohols to glycosyl iodides 3. Glycosyl iodides in solid phase oligosaccharide synthesisen_US
dc.creatorHadd, Michael Josephen_US
dc.contributor.authorHadd, Michael Josephen_US
dc.date.issued1998en_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.abstractThe usefulness of glycosyl iodides in carbohydrate chemistry has been demonstrated. Both anionic and neutral nucleophiles have been shown to react readily with glycosyl iodides as the glycosyl donor. High yields and stereoselectivity were obtained along with short reaction times. Anionic nucleophiles gave β glycosides selectively, whereas neutral nucleophiles gave α glycosides in the presence of tetrabutylammonium iodide. Initial investigation of the applicability of these glycosidation conditions to solid phase oligosaccharide synthesis has been accomplished.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectChemistry, Organic.en_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.advisorGervay, Jacquelynen_US
dc.identifier.proquest9831839en_US
dc.identifier.bibrecord.b38646754en_US
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