The stereoselective synthesis of cyclopropylphosphonate analogs of nucleotides

Tetrahedron Letters

Volumn 40, Issue 47, 1999, Pages 8235-8238

  Hah, Jung Hwan ^a   Gil, Jun Mo ^a   Oh, Dong Young ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; PHOSPHONIC ACID DERIVATIVE; PURINE NUCLEOTIDE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0033584922     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01747-5     Document Type: Article

References (27)

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18. 4P: 284.1177; found: 284.1175.
19. The reaction of 2f and MCPBA yielded 3f, but it was spontaneously cyclized to give 2-hydroxymethyl-4-phosphonyl- 5-(4-chlorophenyl)-2,3-dihydrofuran by action of sodium bicarbonate which was added in the work-up step to remove unreacted MCPBA.
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25. 3P: 325.1304; found: 325.1301.
26. A couple of the attempted azide substitutions of 5b led to the formation of two inseparable mixtures, including an azide- substituted product.
27. A few related examples describe the nucleotide analogs bearing a cyclopropane ring just as a pendant, not as a replacement of the furanose ring. Yu, K.-L.; Bronson, J. J.; Yang, H.; Patick, A.; Alam, M.; Brankovan, V.; Datema, R.; Hitchcock, M. J. M.; Martin, J. C. J. Med. Chem. 1993, 36, 2726.