Highly Efficient Syntheses of Hyaluronic Acid Oligosaccharides
β Scribed by Lijun Huang; Xuefei Huang
- Publisher
- John Wiley and Sons
- Year
- 2007
- Tongue
- English
- Weight
- 260 KB
- Volume
- 13
- Category
- Article
- ISSN
- 0947-6539
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β¦ Synopsis
Abstract
Highly efficient syntheses of hyaluronic acid oligosaccharides have been accomplished through the preβactivation based iterative oneβpot strategy. A series of oligosaccharides ranging from diβ to hexasaccharides were rapidly assembled using only near stoichiometric amounts of the building blocks without aglycon adjustment or purifications of intermediate oligosaccharides. Deprotection and oxidation protocols were developed for protective group removal and oxidationβstate adjustment. The availability of such structurally well defined synthetic hyaluronic acid oligosaccharides will greatly facilitate the establishment of detailed structureβfunction relationships.
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Efficient synthesis of 1-, 4-, and 5-caffeoylquinic acid was achieved in three or four steps with suitably protected quinic acid precursors, in overall yields of 41%, 36%, and 60% [from quinic acid (1)]. 1-Caffeoylquinic acid was prepared by esterification of acetone quinide 7 with caffeoyl chloride
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