Major simplifications in oligosaccharide syntheses arising from a solid-phase based method: An application to the synthesis of the Lewis b antigen Journal Article
| Authors: | Randolph, J. T.; McClure, K. F.; Danishefsky, S. J. |
| Article Title: | Major simplifications in oligosaccharide syntheses arising from a solid-phase based method: An application to the synthesis of the Lewis b antigen |
| Abstract: | Polymer bound glycals, upon activation by epoxidation, function as competent β-glycosyl donors. The first glycal is linked through a silyl ether linker to a commercially available divinylbenzene polystyrene copolymer. At the end of the synthesis, soluble oligosaccharide is retrieved from the polymer by fluoridolysis. The method is self-corrective in that failed donors in a coupling step do not reemerge in the next cycle. The method is particularly powerful for creating branched sugars at C2, a common branching site. An application of the solid phase method to a straightforward synthesis of the Lewis b antigen is described. The superiority of a diisopropylsilyl spacer relative to the previously employed diphenyl spacer is established (see compounds 4 and 5). © 1995, American Chemical Society. All rights reserved. |
| Keywords: | unclassified drug; methodology; antigen; blood group lewis system; carbohydrate synthesis; blood group; article; lewis b antigen |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 117 |
| Issue: | 21 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 1995-05-31 |
| Start Page: | 5712 |
| End Page: | 5719 |
| Language: | English |
| DOI: | 10.1021/ja00126a012 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 28 August 2018 -- Source: Scopus |
