Synthesis of 1,2-cis-Configurated Glycosylphosphonates
| Autor: | Andrea Vasella, Roger Meuwly |
|---|---|
| Rok vydání: | 1986 |
| Předmět: |
chemistry.chemical_classification
Anomer Stereochemistry Organic Chemistry Nuclear magnetic resonance spectroscopy Biochemistry Phosphonate Catalysis Inorganic Chemistry chemistry.chemical_compound Trimethylsilyl trifluoromethanesulfonate chemistry Aldose Drug Discovery Physical and Theoretical Chemistry |
| Zdroj: | Helvetica Chimica Acta. 69:25-34 |
| ISSN: | 1522-2675 0018-019X |
| DOI: | 10.1002/hlca.19860690105 |
| Popis: | A synthesis of 1,2-cis-configurated, non-isosteric phosphonate analogues of aldose-1-phosphates is described. Treatment of 1-O-acyl-glycoses 1, 7, 13, and 19 with trialkyl phosphite in the presence of trimethylsilyl trifluoromethanesulfonate gave the 1,2-cis-configurated glycosylphosphonates 2, 4, 8, 10, 14, 16, 20, and 22 as the major anomers and the 1,2-trans-configurated glycosylphosphonates 3, 5, 9, 11, 15, 17, 21, and 23 as the minor anomers. The 1,2-cis-configurated phosphonates 4, 10, 16, and 22 were deprotected to give the (β-D-glucopyranosyl)phosphonate 6, the (β-D-mannopyranosyl)phosphonate 12, the (β-D-ribofuranosyl)phosphonate 18, and the (β-D-arabinofuranosyl)phosphonate 24, respectively, in high yields. The preferred formation of 1,2-cis-configurated phosphonates is explained by postulating an equilibrium between the anomeric phosphonium-salt intermediates (such as 25 and 26) and a stabilization of the cis-configurated salts through formation of a pentacoordinated species (such as 28). |
| Databáze: | OpenAIRE |
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