Stereoselective Synthesis of the Equatorial Glycosides of Legionaminic Acid
Popik, O; Dhakal, B; Crich, D
| HERO ID | 5102876 |
|---|---|
| In Press | No |
| Year | 2017 |
| Title | Stereoselective Synthesis of the Equatorial Glycosides of Legionaminic Acid |
| Authors | Popik, O; Dhakal, B; Crich, D |
| Journal | Journal of Organic Chemistry |
| Volume | 82 |
| Issue | 12 |
| Page Numbers | 6142-6152 |
| Abstract | The synthesis of a legionaminic acid donor from N-acetylneuraminic acid in 15 steps and 17% overall yield is described. Activation of the adamantanyl thioglycoside in the donor with N-iodosuccinimide and trifluoromethanesulfonic acid in dichloromethane and acetonitrile at -78 °C in the presence of primary, secondary and tertiary alcohols affords the corresponding glycosides in excellent yield and good to excellent equatorial selectivity. In particular, coupling to the 4-OH of a suitably protected neuraminic acid derivative affords a disaccharide that closely resembles the glycosidic linkage in the polylegionaminic acid from the lipopolysaccharide of the Legionella pneumophila virulence factor. A straightforward deprotection sequence enables conversion of the protected glycosides to the free N,N-diacetyllegionaminic acid glycosides. |
| Doi | 10.1021/acs.joc.7b00746 |
| Pmid | 28530837 |
| Wosid | WOS:000403854500015 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |