Solid-phase stereoselective synthesis of 2'-O-methyloligoribonucleoside phosphorothioates using nucleoside bicyclic oxazaphospholidines

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 18, 1998, Pages 2539-2544

  Guo, MaoJun ^a   Yu, Dong ^a   Iyer, Radhakrishnan P ^a   Agrawal, Sudhir ^a  

^a HYBRIDON INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 OXAZAPHOSPHOLIDINE DERIVATIVE; 2 PYRROLIDINE METHANOL; 2' 2 METHYLOLIGORIBONUCLEOSIDE PHOSPHOROTHIOATE; OLIGODEOXYRIBONUCLEOSIDE PHOSPHOROTHIOATE; UNCLASSIFIED DRUG;

ARTICLE; ENZYME STABILITY; NUCLEAR MAGNETIC RESONANCE; SOLID PHASE EXTRACTION; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG DESIGN; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; OLIGORIBONUCLEOTIDES; STEREOISOMERISM; THIOPHOSPHORIC ACID ESTERS;

EID: 0032558503     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00450-8     Document Type: Article

References (14)

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6. 6. Iyer R. P.; Guo, M. J.; Yu, D.; Agrawal, S. Tetrahedron Lett. 1998, 39, 2491.
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8. 8. Iyer, R. P.; Yu, D.; Habus, I.; Ho, N-H.; Johnson, S.; Devlin, T.; Jiang, Z.; Zhou, W.; Xie, J.; Agrawal, S. Tetrahedron 1997, 55, 2731.
9. 9. The absolute configurations of 5, and 6 have not been assigned as yet.
10. 31P NMR was recorded on a Varian 600 MHz NMR Spectrometer; 5a: δ 152.56 ppm, 6a: δ 154.30 ppm.
11. 11. The synthesis was done on a PerSeptive Expedite Nucleic Acid Synthesizer using a slightly modified 1 μM. scale synthesis program.
12. 12. Iyer, R. P.; Regan, J. B.; Egan, W.; Beaucage, S. L. J. Am. Chem. Soc. 1990, 112, 1253.
13. 13. As ascertained by trityl yields.
14. 14. HPLC was done on a Waters 600E instrument using 8NV C-18 4μ Radial Pak cartridge column, gradient (100% A to 60% B over 60 minutes) of buffer A (0.1 M ammonium acetate) and buffer B (80/20, v/v, acetonitrile/ammonium acetate), at a flow rate of 1.0 ml/min.