Synapse - Nucleosides. 132. Synthesis of 5–(2' '-deoxy-β-D-arabinofuranosyl)-1-methyluracils from 1-methyl-ψ-uridine. The first direct introduction of the 2'-substituent to C-2' in the “up” configuration by nucleophilic reactions. Studies directed toward the synthesis of 2'-deoxy 2'-substituted arabino nucleosides 31

Nucleosides. 132. Synthesis of 5–(2' '-deoxy-β-D-arabinofuranosyl)-1-methyluracils from 1-methyl-ψ-uridine. The first direct introduction of the 2'-substituent to C-2' in the “up” configuration by nucleophilic reactions. Studies directed toward the synthesis of 2'-deoxy 2'-substituted arabino nucleosides 31 Journal Article

Authors:	Pankiewicz, K. W.; Kim, J. H.; Watanabe, K. A.
Article Title:	Nucleosides. 132. Synthesis of 5–(2' '-deoxy-β-D-arabinofuranosyl)-1-methyluracils from 1-methyl-ψ-uridine. The first direct introduction of the 2'-substituent to C-2' in the “up” configuration by nucleophilic reactions. Studies directed toward the synthesis of 2'-deoxy 2'-substituted arabino nucleosides 31
Abstract:	A general method is developed for the synthesis of pyrimidine C-nucleosides containing the 2'-substituted-2'-deoxyarabinofuranosyl moiety from a preformed ribo C-nucleoside by direct nucleophilic displacement reactions. 1-Methyl-ψ-uridine (1) was converted to the 2',3'-O-acetonate 2 which was mesylated to 3. Treatment of 3 in aqueous acetic acid gave 5'ψ-uridine (4) which was converted in three steps to 4,5'ψ-uridine (7) via the 2',3'-O-carbonate 5 and the anhydro C-nucleoside 6. 3'-O-Acetyl-2'-O-triflyl-4,5'-anhydro-ψ-uridine (8) was prepared in two steps from 7. The 2'-triflate function was directly displaced by various nucleophiles by treatment with LiCl, LiBr, NaN3, and NaOAc to afford the corresponding 4,5'-anhydro C-nucleosides (9) with the 2'-substituent in the “up” arabino configuration. The anhydro linkage of 9 was readily hydrolyzed by treatment with Dowex 50 (H+) in aqueous solution to give the respective '-deoxy-2'β-D-arabinofuranosyl)-1-methyluracils (10). © 1985, American Chemical Society. All rights reserved.
Keywords:	nonhuman; mass spectrometry; drug synthesis; nuclear magnetic resonance; theoretical study; drug identification; drug analysis; 1 methyl 2' deoxyuracil 5 arabinoside derivative; 1 methyl 2' deoxyuridine; pyrimidine c nucleoside
Journal Title:	Journal of Organic Chemistry
Volume:	50
Issue:	18
ISSN:	0022-3263
Publisher:	American Chemical Society
Date Published:	1985-09-01
Start Page:	3319
End Page:	3322
Language:	English
DOI:	10.1021/jo00218a014
PROVIDER:	scopus
DOI/URL:	https://www.scopus.com/inward/record.uri?eid=2-s2.0-0021995558&doi=10.1021%2fjo00218a014&partnerID=40&md5=db45f640b9bb78dff283c289f7531619
Notes:	Article -- Export Date: 26 October 2021 -- Source: Scopus

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125 Watanabe
43 Pankiewicz

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