Stereoselective synthesis of some 3-nitroglucopyranosyladenine analogues via a nitroolefin intermediate as potential therapeutic agents

Nucleosides and Nucleotides

Volumn 17, Issue 4, 1998, Pages 745-758

  Tsuboike, Kazunari ^a   Minamoto, Katsumaro ^a   Mizuno, Gen ^a   Yanagihara, Kazufomi ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b NISSAN CHEMICAL INDUSTRIES LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

9 (4,6 O BENZYLIDENE 3 DEOXY BETA D HEXOPYRANOSYL)ADENINE; ADENINE DERIVATIVE; ALKENE DERIVATIVE; AMINE; GLUCOPYRANOSIDE; NUCLEOSIDE; SODIUM AZIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0031897363     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319808004672     Document Type: Article

References (12)

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4. 5
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8. An attempt to isolate compound 6 as a hydrochloride salt has also failed.
9. Biffin, M. E. C.; Miller, J.; Paul, D. B. "The chemistry of azido group", ed. by Patai, S., Interscience Publishers, 1971, p. 57.
10. Yamamoto, T.; Tsuboike, K.; Minamoto, K. Nucleic Acids Symp. Series, 1996, 35, 35-36.
11. 3). However, repeated elemental analyses gave no satisfactory analysis values for this compound probably owing to thermal change to 11. In fact, its partial conversion into 11 was observed by TLC after being heated in MeOH for 30 min. Probably, the more electronegative adenine base would make H-3 more labile, thus rendering the azide insertion of the initially formed Michael adduct more facile. Polarity or basisity of the reaction medium may also influence the insertion. Elimination of nitrous acid from iv would occur rapidly to effect resonance stabilization.
12. Huryn, D. M.; Okabe, M. Chem. Rev., 1992, 92, 1745-1768.