Synthesis of C-Linked Glycopyranosyl Serines via a Chiral Glycine Enolate Equivalent
| Autor: | Ernest G. Nolen, Micah M. Watts, Daniel J. Fowler |
|---|---|
| Rok vydání: | 2002 |
| Předmět: |
chemistry.chemical_classification
Alkylation Stereochemistry organic chemicals Monosaccharides Organic Chemistry Glycine Glycopeptides Galactosides Biochemistry Amino acid chemistry.chemical_compound Glucosides chemistry Acetylation Serine Peptide synthesis Stereoselectivity Glycosides Physical and Theoretical Chemistry Glycoconjugates |
| Zdroj: | Organic Letters. 4:3963-3965 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol026839w |
| Popis: | [formula: see text] The stereoselective preparation of C-linked D-gluco- and D-galactopyranosyl L-serines in their alpha and beta forms is herein reported. The syntheses require the conversion of the allyl C-glycopyranosides into their iodoethyl derivatives, which then undergo substitution with the Williams' chiral glycine enolate equivalent. Deprotection and acetylation affords Boc-protected amino acids for peptide synthesis. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|