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Expeditious Synthesis of β-Linked Glycosyl Serine Methylene Isosteres (β-C-Gly Ser) via Ethynylation of Sugar Lactones
| Content Provider | Scilit |
|---|---|
| Author | Dondoni, Alessandro Mariotti, Giandomenico Marra, Alberto Massi, Alessandro |
| Copyright Year | 2001 |
| Description | The addition of the lithium derivative of N-Boc 4-ethynyl-2,2-dimethyl-1,3-oxazolidine to tetra-O-benzyl-d-gluco- and galactonolactone and 2-azido-2-deoxy congeners afforded the corresponding ethynyl ketoses in fairly good yields (64-78%). Following the conversion of the ketoses into O-acetates and removal of the acetoxy group by silane reduction, the resulting β-linked ethynyl glycosides were transformed into N-Boc C-glycosyl α-aminobutyric acids by reduction of the triple bond using $H_{2}/Pd(OH)_{2}$ and oxidative cleavage of the oxazolidine ring using the Jones’ reagent. After the removal of O-benzyl groups of the carbohydrate moieties by hydrogenation and the reduction of azido to amino group, all compounds were subjected to acetylation and isolated as O- and N-acetyl derivatives. The C-glycosyl α-amino acids prepared correspond to methylene isosteres of O-glycosyl serines. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2001-18058.pdf |
| Ending Page | 2137 |
| Page Count | 9 |
| Starting Page | 2129 |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/s-2001-18058 |
| Journal | Synthesis |
| Issue Number | 14 |
| Volume Number | 2001 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2001-01-01 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry Alkynyl Glycosides C-glycosyl Amino Acids |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
