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
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  1. Kyoichi A Watanabe
    125 Watanabe