Synthesis of unsaturated silicon analogues of acyclonucleosides

Tetrahedron Letters

Volumn 39, Issue 23, 1998, Pages 4025-4028

  Latxague, Laurent ^a   Thibon, Jacques ^a   Déléris, Gérard ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE ANALOG;

ARTICLE; DRUG SYNTHESIS; LIPOPHILICITY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0032482502     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00681-9     Document Type: Article

References (13)

1. 1. Cohen, J. S., Ed. Oligodeoxynucleotides as Antisense Inhibitors of Gene Expression; CRC Press; Bocca Raton, FL, 1987.
2. 2. Latxague, L.; Thibon , J.; Guillot, C.; Moreau S.; Déléris, G. Tetrahedron Lett. 1994, 35, 5869-5872.
3. 3. Thibon, J.; Latxague, L.; Déléris, G. J. Org. Chem. 1997, 62, 4635-4642.
4. 4. Unpublished results Dr. S. Moreau, INSERM ; bold letters give the position of the various substitutions: TGAACGAAACTGTGTT, TGAACGAAACTGTGTT AND TGAACGAAACTGTGTT.
5. 5. Schneider, K. C.; Benner, S. A. J. Am. Chem. Soc. 1990, 112, 453.
6. 2), 151.22 (C-2 thymine), 164.44 (C-4 thymine); MS (FAB) m/e 223.4 (100) [M-22]+, 255.4 (100) [M+1]+, 237.4 (76) [M-14] exact: 254.2.
7. 2), 151.43 (C-2 thymine), 164.40 (C-4 thymine); MS (FAB) m/e 255.7 [M-15]+, 271.4 [M+1]+, exact: 270.1.
8. 8. Ghosh, A; Ritter, A. R.; Miller, M. J. J. Org. Chem. 1995, 60, 5808-5813.
9. 9. Gunderson, L.-L.; Benneche, T.; Undheim, K. Tetrahedron Lett. 1992, 33, 1085-1088.
10. 10. Trost, B. M.; Verhoven, T. R. in Comprehensive Organometallic Chemistry, Pergamon, New York, 8, 799-938, 1982.
11. 2O), 110.76 (C-5 thymine), 130.62 (CHSi), 140.26 (C-6 thymine), 140.65 (CH=CHSi), 151.15 (C-2 thymine), 164.76 (C-4 thymine).
12. 2), 151.24 (C-2 thymine), 164.67 (C-4 thymine); MS (FAB) m/e 255.1 (95) [M+1]+, 223.0 (100) [M-31]+, exact: 254.3.
13. 2), 151.17 (C-2 thymine), 164.93 (C-4 thymine); MS (FAB) m/e 271.4 (100) [M+1]+, 293.3 (93) [M+23]+; HRMS (FAB+) found: 271.111157 exact: 271.111411.