The synthesis of 6,6′‐cyclo‐6′‐deoxyhexofuranosyluracils via a diazomethane‐promoted ring‐enlargement reaction Journal Article
| Authors: | Sasson, I. M.; Otter, B. A. |
| Article Title: | The synthesis of 6,6′‐cyclo‐6′‐deoxyhexofuranosyluracils via a diazomethane‐promoted ring‐enlargement reaction |
| Abstract: | The protected 5′‐oxo‐6,5′‐cyclouridine 13 reacts with diazomethane to afford mostly the spiro‐epoxide 18 (79%), but it also undergoes ring‐expansion to give the corresponding 5′‐oxo‐6,6′‐cyclonucleoside 16. Under the conditions of the reaction, ketone 16 reacts further with diazomethane to give the enol ether 20 (12% overall), the isomeric 4‐methoxy nucleoside 15 (2%), and the spiro‐epoxide 19 (4.4%). Acid hydrolysis of the enol ether 20, followed by reduction of the resulting ketone with sodium borohydride, affords a separable mixture of the 5′S (L‐talo) and 5′R (D‐allo) methylene‐bridged cyclonucleosides 7 and 8, respectively. From proton nmr measurements, it appears that the 6′‐methylene groups of these cyclonucleosides project towards the 2′,3′‐edge of the furanose ring. Copyright © 1987 Journal of Heterocyclic Chemistry |
| Keywords: | unclassified drug; nonhuman; drug structure; drug synthesis; nuclear magnetic resonance; theoretical study; 6' deoxy 6,6' cyclouracil beta alloside |
| Journal Title: | Journal of Heterocyclic Chemistry |
| Volume: | 24 |
| Issue: | 5 |
| ISSN: | 0022-152X |
| Publisher: | Wiley-Blackwell Publishing, Inc. |
| Date Published: | 1987-09-01 |
| Start Page: | 1439 |
| End Page: | 1444 |
| Language: | English |
| DOI: | 10.1002/jhet.5570240543 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 5 February 2021 -- Source: Scopus |
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