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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