4.4 Article

Thieme Chemistry Journal Awardees - Where are They Now? Synthesis of the Marine Glycolipid Dioctadecanoyl Discoside

Journal

SYNLETT
Volume -, Issue 19, Pages 3099-3102

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1218301

Keywords

marine sponge; glycolipid; mannose; glycosylation; inositol

Funding

  1. EPSRC/University
  2. Royal Society
  3. AstraZeneca
  4. BBSRC
  5. St Hugh's College, Oxford
  6. EPSRC National Mass Spectrometry Service Centre, Swansea
  7. University of St Andrews NMR and Mass Spectrometry Services
  8. Biotechnology and Biological Sciences Research Council [BB/C515255/1] Funding Source: researchfish

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The first synthesis of the inositol-containing marine glycolipid dioctadecanoyl discoside is reported. The key glycosylation reaction proceeds with beta-selectivity at reduced temperature. The separable anomers could be readily progressed to afford discoside, its peracetate and the unnatural beta-derivatives.

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