A novel strategy toward the synthesis of N-(β-glycosyl)asparagines based on the alkylation of ethyl nitroacetate using N-(β-glycosyl)iodoacetamides
| Autor: | Laxminarayan Sahoo, Duraikkannu Loganathan, Katuri J.V. Paul |
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| Rok vydání: | 2010 |
| Předmět: |
crystal structure
synthesis Stereochemistry chirality n (beta glycosyl)asparagine derivative Alkylation n (9 anthracenylmethyl)cinchoninium chloride Biochemistry chemistry.chemical_compound Drug Discovery Glycosyl Asparagine anthracene derivative alkylation ethylnitroacetic acid Organic Chemistry stereochemistry Absolute configuration Diastereomer acetamide derivative structure analysis unclassified drug chemistry Yield (chemistry) acetic acid derivative lipids (amino acids peptides and proteins) asparagine derivative n (beta glycosyl)iodoacetamide derivative Derivative (chemistry) Conjugate |
| Zdroj: | Tetrahedron Letters. 51:5713-5717 |
| ISSN: | 0040-4039 |
| DOI: | 10.1016/j.tetlet.2010.08.072 |
| Popis: | A conceptually novel strategy has been developed for the synthesis of N-(?-glycosyl)asparagine precursors in good yield by the alkylation of ethyl nitroacetate using six per-O-acetylated N-(?-glycosyl)iodoacetamides derived from mono- and disaccharides. The use of a chiral organocatalyst, N-(9-anthracenylmethyl)cinchoninium chloride (10 mol %), resulted in diastereoselective alkylation up to 64% de. Single crystal structure analysis of the purified major diastereomer of the Glc derivative revealed an absolute configuration of S at the ?-carbon of the monosubstituted ethyl nitroacetate which is a precursor of the l-asparagine conjugate. � 2010 Elsevier Ltd. All rights reserved. |
| Databáze: | OpenAIRE |
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