利什曼原虫脂磷聚糖(LPG)相关四糖合成砌块的高效合成研究

声明

CATALOGUE

LIST OF SCHEMES 合成路线列表

摘要

Abstract

Abbreviations 缩略语说明

Chapter 1: Introduction

1.1 General Overview

1.2 Study Significance

1.3 Objectives

1.4 Outlines

Chapter 2: Background Literature Review

2.1 Life Cycle of the Leishmania Parasite

2.2 Epidemiology of Leishmaniasis

2.3 Pathology of Leishmaniasis

2.3.1 Visceral Leishmaniasis (VL)

2.3.2 Mucocutaneous Leishmaniasis (MCL)

2.3.3 Cutaneous Leishmaniasis (CL)

2.4 Drugs for Leishmaniasis

2.5 Vaccination Approach

2.6 New Synthetic Vaccines Based on Leishmania Cell Wall

Chapter 3: The Components of Leishmania LPG

3.1 Glycosylphosphatidylinositol (GPI) Anchor

3.2 Phosphosaccharide Glycan Core

3.3 LPG Phosphoglycan Repeating Units

3.4 Leishmania LPG Tetrasaccharide Cap

Chapter 4: Synthetic Approaches of Tetrasaccharide Cap of Leishmania LPG

4.1 Solution and Solid-Support Synthesis Method

4.1.1 Automated solid-phase synthesis of Leishmania cap tetrasaccharide

4.1.2 Solution-phase synthesis

4.2 n-Pentenyl Glycosylation Protocol

4.3 One-Pot Sequential Glycosylation

4.4 AuBr3 Mediated Glycosidation

Chapter 5: Results , Discussion, and the Experimental Part

5.1 General Methods

5.2 General Scheme

5.3 Chemical Synthesis ofthe Acceptor Building Block

5.3.1 Chemical synthesis of compound 2

5.3.2 Chemical synthesis of compound 3

5.3.3 Chemical synthesis of compound 4

5.3.4 Chemical synthesis of the intermediate compound I.Ml

5.3.5 Chemical synthesis of compound I.M2 and compound 5

5.3.6 Chemical synthesis of compound 6

5.3.7 Chemical synthesis of compound 7

5.3.8 Chemical synthesis of compound 10

5.3.9 Chemical synthesis of compound 8

5.3.10 Chemical synthesis of compound 9

5.4 Chemical Synthesis ofDonor

5.4.1 Chemical s严lthesis of compound 12

5.4.2 Chemical synthesis of compound 13

5.4.3 Chemical synthesis of compound 14

5.4.4 Chemical synthesis of compound 15

5.5 Chemical Synthesis of Disaccharide 16

5.6 Preparation ofthe Chemical Synthesis ofTetrasaccharide Cap

5.6.1 Chemical synthesis of disaccharide acceptor 17

5.6.2 General scheme for the chemical synthesis oftrisaccharide donor

5.6.3 Chemical synthesis ofthe tetrasaccharide cap (next steps)

Chapter 6: Summary and Prospect

Appendix

References

Acknowledgment

List of Publications

List of Synthesized Chemical Compounds