Abstract
This dissertation describes the synthesis of a 3-O-sulfonated octasaccharide that binds with HSV-1. Chapter 1 introduces the cell surface glycoconjugates and explains the biochemical function of heparin/heparan sulfate. The literature reports about the synthesis of heparan sulfate octasaccharides, which bind HSV-1 are summarized in Chapter 2. Chapter 3 initially introduces the synthetic challenges regarding the synthesis of the desired octasaccharide 3. A retrosynthetic plan following the construction of the octasaccharide skeleton in a [3 + 5] manner is then presented. Chapter 4 provides a detailed description of the preparation of the fully-protected octasaccharide 52 through the assemblies and couplings of the glycosyl donor 43, the N,N-diacetyl derivative 106, and the glycosyl acceptor 51. Using deuterium-labeled compounds, the mechanism of the reductive ring opening of benzylidene acetals is also clarified herein.Chapter 5 describes the preparation of the octasaccharide 3 from fully-protected octasaccharide 52 followed by eleven functional roup transformation steps. The conclusions of this dissertation work are summarized in Chapter 6. Lately, chapter 7 provides the detailed experiment procedure and the physical data of the compounds synthesized herein.