Gram-scale syntheses of the (1 → 3)-linked and (1 → 4)-linked hyaluronan disaccharides
| Autor: | Sara L. Adamski-Werner, Bryan K. S. Yeung, Lynne A Miller-Deist, Peter A. Petillo |
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| Rok vydání: | 2004 |
| Předmět: |
Carbamate
Molecular Structure medicine.medical_treatment Organic Chemistry Acetal Disaccharide Hypochlorite General Medicine Uronic acid Disaccharides Cleavage (embryo) Biochemistry Acetonide Analytical Chemistry chemistry.chemical_compound chemistry Yield (chemistry) medicine Organic chemistry Hyaluronic Acid |
| Zdroj: | Carbohydrate Research. 339:1255-1262 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/j.carres.2004.03.005 |
| Popis: | The first gram-scale syntheses of two hyaluronan disaccharides are described. Construction of the (1 → 4)-linked disaccharide 12 was achieved in 12% overall yield using 2,3-bis-dimethyl acetal protection in combination with chlorosilane-induced carbamate cleavage methodologies. The uronic acid functionality was installed using TEMPO oxidation with NaOCl as the hypochlorite source. The (1 → 3)-linked disaccharide 18 was achieved in 7% overall yield utilizing acetonide protection in addition to the chlorosilane-induced carbamate cleavage methodology and the TEMPO oxidation. |
| Databáze: | OpenAIRE |
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