Application of glycals to the synthesis of oligosaccharides: Convergent total syntheses of the Lewis X trisaccharide sialyl Lewis X antigenic determinant and higher congeners Journal Article
| Authors: | Danishefsky, S. J.; Gervay, J.; Peterson, J. M.; McDonald, F. E.; Koseki, K.; Griffith, D. A.; Oriyama, T.; Marsden, S. P. |
| Article Title: | Application of glycals to the synthesis of oligosaccharides: Convergent total syntheses of the Lewis X trisaccharide sialyl Lewis X antigenic determinant and higher congeners |
| Abstract: | Exploiting the differences in reactivity of the hydroxyl groups of glucal allows for rapid access to the sLex tetrasaccharide glycal. This compound is readily converted to the title compounds by azaglycosylation followed by deprotection. The use of stannyl alkoxides in the glycosylation—rearrangement step allows for the use of minimally protected glycosides as the glycosyl acceptors. Employing a galactal epoxide as a glycosyl donor allows for a maximally convergent synthesis of the Lex glycal. © 1995, American Chemical Society. All rights reserved. |
| Keywords: | unclassified drug; methodology; epitope; reaction analysis; oligosaccharide; carbohydrate synthesis; article; sialyl lewis x antigen determinant |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 117 |
| Issue: | 7 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 1995-02-22 |
| Start Page: | 1940 |
| End Page: | 1953 |
| Language: | English |
| DOI: | 10.1021/ja00112a007 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 28 August 2018 -- Source: Scopus |
