Synthesis of [R-(R*,S*)]- and [S-(R*,R*)]-β-Hydroxy-3-(β-D-ribofuranosyl)- wybutines, the most probable alternatives for the hypermodified nucleoside of rat liver phenylalanine transfer ribonucleic acid

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 1979-1982

  Itaya, Taisuke ^a   Kanai, Tae ^a   Iida, Takehiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; GLYCOSYLATION; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031575737     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00253-0     Document Type: Article

References (11)

1. 1. Itaya, T.; Mizutani, A.; Iida, T. Chem. Pharm. Bull. 1991, 39, 1407-1414.
2. 2. Kasai, H.; Yamaizumi, Z.; Kuchino, Y.; Nishimura, S. Nucleic Acids Res. 1979, 6, 993-999.
3. 3. Itaya, T.; Watanabe, N.; Iida, T.; Kanai, T.; Mizutani, A. Tetrahedron 1995, 51, 6419-6430.
4. 4. Itaya, T.; Morisue, M.; Shimomichi, M.; Ozasa, M.; Shimizu, S.; Nakagawa, S. J. Chem. Soc., Perkin Trans. 1 1994, 2759-2765.
5. 5. Itaya, T.; Morisue, M.; Takeda, M.; Kumazawa, Y. Chem. Pharm. Bull. 1990, 38, 2656-266
6. 4
7. 7. Glemarec, C.; Wu, J.-C.; Remaud, G.; Bazin, H.; Oivanen, M.; Lönnberg, H.; Chattopadhyaya, J. Tetrahedron 1988, 44, 1273-1290.
8. 8. Itaya, T.; Iida, T.; Shimizu, S.; Mizutani, A.; Morisue, M.; Sugimoto, Y.; Tachinaka, M. Chem. Pharm. Bull. 1993, 41, 252-261.
9. 2Me), 4.10 [3H, s, overlapping with a 1H signal arising from C(4′)-H at 4.11, N(4)-Me], 4.19 [1H, d, J = 4 Hz, C(3′)-H], 4.37 [1H, dd, J = 4 and 7.5 Hz, C(2′)-H], 5.12 [1H, br, C(α)-H], 5.53 (1H, br, NH), 5.85 [1H, br d, J = 16 Hz, C(β)-H], 6.21 [1H, d, J = 7.5 Hz, C(1′)-H], 7.74 [1H, d, J = 16 Hz, C(γ)-H], 7.91 [1H, s, C(2)-H].
10. 2], 3.99 [1H, ddd, J = 3.4, 3.4, and 4.9 Hz, C(4′)-H], 4.04 [3H, s, N(4)-Me], 4.09 [1H, m, C(β)-H], 4.11-4.16 [2H, m, C(α)-H and C(3′)-H], 4.45 [1H, ddd, J = 4.4, 5.9, and 4.9 Hz, C(2′)-H], 5.06 [1H, d, J = 5.9 Hz, C(β)-OH], 5.12 [1H, dd, J = 5 Hz each, C(5′)-OH], 5.32 [1H, d, J = 5.4 Hz, C(3′)-OH], 5.71 [1H, d, J = 5.9 Hz, C(2′)-OH], 6.11 [1H, d, J = 4.9 Hz, C(1′)-H], 7.28 (1H, d, J = 8.3 Hz, NH), 8.22 [1H, s, C(2)-H].
11. 2O-MeOH (70:30, v/v) (retention time: 21.9 and 17.8 min) as eluent at the flow rate of 0.5 ml per min and room temperature.