Nucleosides. 134. 3'-amino-3'-deoxy-β-D-hexopyranosyl nucleosides. 8. Synthesis of 2,3'-Imino nucleosides by solvolysis of 2'-O-mesylglucosyluracil derivatives Journal Article
| Authors: | Matsuda, A.; Watanabe, K. A. |
| Article Title: | Nucleosides. 134. 3'-amino-3'-deoxy-β-D-hexopyranosyl nucleosides. 8. Synthesis of 2,3'-Imino nucleosides by solvolysis of 2'-O-mesylglucosyluracil derivatives |
| Abstract: | Treatment of 1-(3'-acetamido-3'-deoxy-2'4'-di-O-mesyl-β-D-glucopyranosyl)uracil (1) with sodium acetate in aqueous methylcellosolve afforded '-amino-3'-deoxy-β-D-talopyranosyl)uracil and '-amino-3'-deoxy-β-D-talopyranosyl)isocytosine in almost equal amounts. These products were separated and characterized as their corresponding peracetyl derivatives 2 and 3. The manno isomer 10 and the 6'-deoxy analogue 19 of 3 were also synthesized by solvolysis of '-deoxy-2'-O-mesyl-β-D-glucopyranosyl)uracil trifluoroacetic acid salt (8) and 1-(3'-acetamido-3',6'-dideoxy-2'4'-β-O-mesyl-β-D-glucopyranosyl)uracil (17), respectively. A plausible mechanism for the formation of the 2,3'-imino linkage is discussed. © 1985, American Chemical Society. All rights reserved. |
| Keywords: | nonhuman; drug synthesis; nuclear magnetic resonance; theoretical study; drug identification; uracil derivative; ultraviolet spectrophotometry; drug analysis; 3' amino 3' deoxy 2,3' iminoisocytosine 1 beta talopyranoside; 3' amino 3' deoxyuracil 1 beta talopyranoside |
| Journal Title: | Journal of Organic Chemistry |
| Volume: | 50 |
| Issue: | 15 |
| ISSN: | 0022-3263 |
| Publisher: | American Chemical Society |
| Date Published: | 1985-07-01 |
| Start Page: | 2660 |
| End Page: | 2664 |
| Language: | English |
| DOI: | 10.1021/jo00215a013 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 26 October 2021 -- Source: Scopus |
