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Volumn 9, Issue 9, 2001, Pages 2315-2322

The case for configurational stability of H-phosphonate diesters in the presence of diazabicyclo[5.4.0]undec-7-ene (DBU)

Author keywords

[No Author keywords available]

Indexed keywords

DIAZABICYCLO(5.4.0)UNDEC 7 ENE; DINUCLEOSIDE PHOSPHATE; H PHOSPHONATE DIESTER; NUCLEOSIDE; PHOSPHATE; PHOSPHORUS; UNCLASSIFIED DRUG;

EID: 0034830540     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(01)00140-7     Document Type: Article
Times cited : (14)

References (46)
  • 1
    • 0003641058 scopus 로고    scopus 로고
    • Stawinski, J. In Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Dekker: New York, 1992; pp 377-434.
  • 25
    • 0003565780 scopus 로고    scopus 로고
    • Seela, F.; Kretschmer, U. J. Chem. Soc. Chem. Commun. 1990, 1154-1159
  • 29
    • 0003565782 scopus 로고    scopus 로고
    • In the original publications the authors erroneously referred to this and the related reactions as stereospecific instead of stereoselective ones.
  • 30
    • 0003563130 scopus 로고    scopus 로고
    • The reaction occurs with retention of configuration at the phosphorus center, but the priority rules of the CIP notation of absolute configuration lead in this instance to a formal change of the sense of chirality at the P-atom.
  • 31
    • 0003565784 scopus 로고    scopus 로고
    • This problem will be addressed separately on another occasion.
  • 35
    • 0003564956 scopus 로고    scopus 로고
    • Johansson, T.; Bollmark, M.; Stawinski, J. In Collection Symposium Series; Holy, A., Hocek, M., Eds.; Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic: Prague, 1999; Vol. 2; pp 75-78.
  • 36
    • 0003569854 scopus 로고    scopus 로고
    • At the initial stages of this project, there was a remote possibility that the reported stereoselectivity during sulfurisation of 1 could be due to configurational instability of phosphorothioates 2 in the presence of DBU. In a separate experiment, we found that this was not the case.
  • 37
    • 0003712950 scopus 로고    scopus 로고
    • 31P NMR resonances from diastereomeric dinucleoside phosphorothioates 2.
  • 38
    • 0003565786 scopus 로고    scopus 로고
    • 1H coupled spectra, and by comparison with authentic samples, prepared as described in the Experimental.
  • 40
    • 0003640823 scopus 로고    scopus 로고
    • P (ca. 10%).
  • 43
    • 0003712952 scopus 로고    scopus 로고
    • P=7.54 and 8.31ppm) is probably erroneous and refers most likely to its decomposition product, i.e., H-phosphonate 1 diastereomers.
  • 44
    • 0003608302 scopus 로고    scopus 로고
    • Under such conditions, the major (or the sole) product of the reaction was apparently the corresponding tetranucleoside 1-(phosphinoxy)benzylphosphonate formed via the reaction of H-phosphonate 1 (generated from 3) with benzoylphosphonate 3, followed by the rearrangement of the produced symmetrical tetranucleoside bisphosphonate. See also: Fitch, S. J.; Moedritzer, K. J. Am. Chem. Soc. 1962, 84, 1876.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.