Improved synthesis of oligonucleoside methylphosphonate analogs

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 12, 1996, Pages 1393-1398

  Habus, Ivan ^a   Devlin, Theresa ^a   Iyer, Radhakrishnan P ^a   Agrawal, Sudhir ^a  

^a HYBRIDON INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 PENTENOIC ACID; METHYLPHOSPHONIC ACID; METHYLPHOSPHONIC ACID DERIVATIVE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEIC ACID SYNTHESIS; NUCLEOTIDE SEQUENCE;

EID: 0029950562     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00239-9     Document Type: Article

References (18)

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10. For a review of phosphoramidite chemistry, see: Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223.
11. (a) The PNT protecting group was first used in the synthesis of amino sugars, see: Debenham, J. S.; Madsen, R.; Roberts C.; Fraser-Reid, B. J. Am. Chem. Soc. 1995, 117, 3302;
12. (b) Iyer, R. P.; Yu, D.; Ho, N.-H.; Devlin, T.; Agrawal, S. J. Org. Chem. 1995, 60, 8132;
13. Iyer, R. P.; Devlin, T.; Habus, I.; Ho, N.-H.; Yu, D.; Agrawal S. Tetrahedron Lett. 1996, 37, 1539.
14. 4OH to effect complete deprotection, especially when synthesizing oligonucleotides. Experiments are under way to gain insight into the mechanism of deprotection using PNT nucleosides. For further enhancement of the rate of deprotection using PNT nucleosides other reagents are also being evaluated.
15. Padmapriya, A. A.; Agrawal, S. Bioorg. Med. Chem. Lett. 1993, 3, 761.
16. (a) For details of HPLC analysis, see: Iyer, R. P.; Yu, D.; Agrawal, S. Bioorg. Chem. 1995, 23, 1.
17. iBu methylphosphonamidite monomers were procured from Glen Research (Sterling, VA).
18. Iyer, R. P.; Egan, W.; Regan, J. B.; Beaucage, S. L. J. Am. Chem. Soc. 1990, 112, 1253.