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Título: Synthetic studies on a(3,6)-mannans and a novel approach to the stereoselective construction of b-mannosides
Autores: Bubenik, Monica.
Fecha: 1997
Publicador: McGill University - MCGILL
Fuente:
Tipo: Electronic Thesis or Dissertation
Tema: Chemistry, Organic.
Descripción: Attempts were made to synthesize cleanly and efficiently a 3,6-branchpoint mannose monomer via three synthetic routes. This monomer was then to be used in a solution-phase synthesis of a high mannose-type nonasaccharide using a PEG soluble polymer support developed in our laboratory. The monomer was to meet the requirements of (1) stable protecting groups on positions 2 and 4; (2) easily cleavable groups on positions 3 and 6; (3) a group which is stable and a good donor on position 1. The key step in the synthesis of the first monomer, containing allyl groups on positions 3 and 6, involved using Ogawa's stannylation methodology. The key step in the second route involved benzylating a monomer containing two ester groups on positions 3 and 6 using Bundel's methodology. The third route, based on well established literature procedures, gave the desired compound in acceptable yield but with more purification effort.
Using a similar approach to that taken independently by Stork and Hindsgaul, attempts were made to construct $ beta$-glycosides using antimony as a temporary connector. (Abstract shortened by UMI.)
Idioma: en