CARB 4 |
| Two methods for the synthesis of N-glycosides (D-gluco-, D-galacto-, D-xylo- and D-ribosides) of 4-hydroxyhexahydropyrimidine-2-thiones were developed. The first one was based on the reaction of peracetylglycosylisothiocyanates with β-aminoketones or acetals of β-aminoaldehydes followed by deprotection. The second method included the reaction of glycosylamines with β-isothiocyanatoaldehydes or β-isothiocyanatoketones. We found that partly protected ribo- and xylofuranosylamines reacted with β-isothiocyanatoaldehydes to give new types of cyclonucleosides containing hydrogenated pyrimidine aglycone. Multi-stage rearrangement of 4,5'-anhydro-4-hydroxy-3-(β-D-ribofuranosyl)hexahydropyrimidine-2-thiones into 4,2'-anhydro-4-hydroxy-3-(α-D-ribofuranosyl)hexahydropyrimidine-2-thiones was discovered and studied. |
|
Nucleosides, Nucleotides and Oligonucleotides
9:00 AM-11:40 AM, Sunday, 10 September 2006 Hilton San Francisco -- Yosemite C, Oral
Division of Carbohydrate Chemistry |