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The synthesis of amino- and deutero- sugars from halo-cyclohexadiene-cis-diols

A versatile method for the preparation of 2-amino-2-deoxy-, 3-amino-3-deoxy-, 4- amino-4-deoxy-, and 5-amino-5-deoxy-sugars from noncarbohydrate precursors, halobenzenes 1 (Figure 1), has been developed.

See: Figure 1: Aminosugar Targets from Halobenzenes

This methodology has also been applied to achieve the synthesis of protected D-mannose- 2,3,4,5,6-d₅ 191, and derivatives thereof, from the metabolite d₅- bromocyclohexadiene-cis-diol 189 obtained from the microbial oxidation of d₅- bromobenzene 2 (Figure 2).

See: Figure 2: Perdeuterated Sugar Synthesis / Ph. D.

Identiferoai:union.ndltd.org:VTETD/oai:vtechworks.lib.vt.edu:10919/38104
Date06 June 2008
CreatorsPitzer, Kevin K.
ContributorsChemistry, Hudlicky, Tomas, Tanko, James M., Gibson, Harry W., Merola, Joseph S., White, Robert H.
PublisherVirginia Tech
Source SetsVirginia Tech Theses and Dissertation
LanguageEnglish
Detected LanguageEnglish
TypeDissertation, Text
Formatx, 186 leaves, BTD, application/pdf, application/pdf
RightsIn Copyright, http://rightsstatements.org/vocab/InC/1.0/
RelationOCLC# 34137657, LD5655.V856_1995.P589.pdf

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