Unprecedented chlorination of 2,2'-anhydro-5,6-dihydropyrimidine nucleosides during DDQ oxidation

Tetrahedron Letters

Volumn 38, Issue 21, 1997, Pages 3683-3686

  Pragnaeharyulu, Palle V P ^a   Abushanab, Elie ^a  

^a UNIVERSITY OF RHODE ISLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; PYRIMIDINE DERIVATIVE;

ARTICLE; CHLORINATION; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030904576     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00727-2     Document Type: Article

References (5)

1. Pragnacharyulu, P. V. P.; Vargeese, C.; McGregor, M.; Abushanab, E. J. Org. Chem. 1995, 60, 3096.
2. Subsequent to our original report (Ref 1), we have found an additional 5′-desilylated 2,2′-anhydrothymidine, raising the overall oxidation yield with DDQ to 95%.
3. Shriner, R. L.; Fuson, R. C.; Curtin, D. Y.; Morrill, T. C. The Systemic Identification of Organic Compounds, John Wiley and Sons: New York, 1980, pp. 81-82.
4. 2O exchangeable).
5. Kelly, J. A.; Driscoll, J. S.; McCormack, J. J.; Roth, J. S.; Marquez, V. E., J. Med. Chem. 1986, 29, 2351. Other isomerization reactions listed in this reference include nucleosides whose glycosidic nitrogen is derived from urea, 5,6-dihydrouracil, aminopyrimidine, and anthranilonitrile.