Synthetic studies in the carbohydrate field

Baker, Archibald James (1961) Synthetic studies in the carbohydrate field. PhD thesis, University of Glasgow.

Abstract

Part I - 2-Deoxy-DL-ribose. Synthetic routes to 2-deoxy-DL-ribose from non-carbohydrate precursors have been investigated and an eight stage synthesis from propargyl alcohol is described. Kojic acid has been elaborated, via a known intermediate, to 2-deoxy-DL-ribose. As an extension of this work a route to the 2,6-dideoxyhexoses from acetylenic precursors is described. Appendix I. The selective addition of hypobromous acid to hex-5-en-2-yn-1-ol is discussed. Appendix II. Some unsuccessful approaches to DL-ribulose from acetylenic precursors have been explored. Part II - Apiose and Cordycepose. A wide variety of synthetic approaches to the branched-chain sugars apiose and cordycepose, from non-carbohydrate precursors, has been studied. The synthesis of 2-phenyl-5-carboxy-1,3-dioxan, a derivative of the saccharinic acid, 4-hydroxy-3-hydroxymethyl propanoic acid which has not hitherto been synthesised, is described. Part III - Rhodosamine. Routes to the amino-sugar rhodosamine from acetylenic precursors are described. An approach from hept-1-en-4-yn-6-ol has given a compound with the gross structure of DL-aldehydo "rhodosamine" diacetate. Anomalous oxidation of an intermediate amine is discussed in the light of recent investigations.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Additional Information: Adviser: Professor R.A. Raphael.
• Keywords: Organic chemistry.
• Subjects: Q Science > QD Chemistry
• Colleges/Schools: College of Science and Engineering > School of Chemistry
• Supervisor's Name: Supervisor, not known
• Date of Award: 1961
• Depositing User: Enlighten Team
• Unique ID: glathesis:1961-79398
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 05 Mar 2020 10:06
• Last Modified: 28 Jul 2021 15:55
• URI: https://theses.gla.ac.uk/id/eprint/79398