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Title: Nucleophilic ring opening studies on Benzyl Anhydroribopyranosides
Researcher: Vasudeva, P K
Guide(s): Nagarajan, M
Keywords: Chemistry
Upload Date: 5-Apr-2011
University: University of Hyderabad
Completed Date: 1996
Abstract: This thesis deals with the ring opening reactions of benzyl 3,4-anhydro-£-D ribopyranoside and benzyl 2,3-anhydro-a-D-ribopyranoside. The thesis consists of four sections, namely, introduction, results, discussion and experimental. The introduction begins with the classification of different sugar epoxides followed by representative examples of ring opening reactions of each class. Reactions of 2,3- and 3,4- anhydrohexopyranosides followed by a detailed survey of alkyl 2,3- and 3,4- anhydroribopyranosides are included to show the versatality of nucleophilic ring opening reactions of epoxides to form simple and rare deoxy sugars. The introduction section concludes with some examples of sugar epoxides as chiral starting materials for the syntheses of biologically active molecules. Earlier work from our laboratory had shown that benzyl 3,4- anhydro-ct-D-ribopyranoside reacted with nucleophiles exclusively at C-3. This result was rationalized based on a repulsive interaction between the entering nucleophile and the electron lone pair on the pyranose oxygen, precluding attack at C-4 and directing it to C-3. To establish the validity of this interpretation, it was thought necessary to study the ring opening reactions of benzyl 3,4-anhydro-£-D-ribopyranoside, wherein the anomeric substituent should now direct opening to C-4 on steric grounds, overriding the effect of the oxygen lone pair.
Pagination: x, 145p.
Appears in Departments:School of Chemistry

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01_title.pdfAttached File30.28 kBAdobe PDFView/Open
02_dedication.pdf16.01 kBAdobe PDFView/Open
03_contents.pdf16.32 kBAdobe PDFView/Open
04_declaration.pdf18.61 kBAdobe PDFView/Open
05_certificate.pdf31.53 kBAdobe PDFView/Open
06_acknowledgements.pdf21.88 kBAdobe PDFView/Open
07_abbreviations.pdf17.75 kBAdobe PDFView/Open
08_abstract.pdf43.42 kBAdobe PDFView/Open
09_chapter 1.pdf931.68 kBAdobe PDFView/Open
10_chapter 2.pdf395.89 kBAdobe PDFView/Open
11_chapter 3.pdf734.78 kBAdobe PDFView/Open
12_chapter 4.pdf397.32 kBAdobe PDFView/Open
13_chapter 5.pdf948.08 kBAdobe PDFView/Open
14_references.pdf116.55 kBAdobe PDFView/Open

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