Synthesis of uracil polyoxin C from uridine

Tetrahedron Letters

Volumn 37, Issue 2, 1996, Pages 163-166

  Evina, Claude Mvondo ^a   Guillerm, Georges ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG; URACIL POLYOXIN C; URIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030034350     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02116-7     Document Type: Article

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21. 3).
22. 4, N-methylmorpholine-N-oxide) or with AD-mix-β gave diastereomeric mixture of 5',6'-diols, respectively in 2:1 and 1:1 ratios. These mixtures were resolved after protection of the C-5′ epimeric diols into their corresponding 5′,6′-O-isopropylidene derivatives.
23. 2 methodology (Allinger, N.L. J. Am. Chem. Soc. 1977, 99, 8127-8134) allowed the determination of the different constraint energies for the preferred conformers of diastereomeric cyclonucleosides 7a and 7b (Scheme 2) and their different 4′-5′ dihedral angles and J4′,5′ coupling constants (7a J4′,5′ 0-2.9 Hz; 7b J4′,5′ 6.1-9 Hz). From this method, it was also predicted a close proximity of the 3′ and 5′ protons (2.82 -3.05 Å) in 7a. Results of these calculations agreed well with observed NOE (15%) between H-3′ and H-5′ and measured J4′,5′ coupling constant (Scheme 2) for the 2,5′-O-cyclonucleoside derivative 7.
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