Nucleosides and nucleotides. 189. Investigation of the stereoselective coupling of thymine with meso-thiolane-3,4-diol-1-oxide derivatives via the Pummerer reaction

Tetrahedron Letters

Volumn 40, Issue 34, 1999, Pages 6297-6300

  Naka, Takashi ^a   Nishizono, Naozumi ^a   Minakawa, Noriaki ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Neighboring group effects; Nucleosides; Puremeter reactions; Thioglycosides

Indexed keywords

NUCLEOSIDE DERIVATIVE; THIOL DERIVATIVE; THYMINE;

ARTICLE; DIASTEREOISOMER; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033588332     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01287-3     Document Type: Article

References (14)

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8. a) O'Neil, I. A.; Hamilton, K. M. Synlett, 1992, 791-792.
9. b) Yoshimura, Y.; Kitano, K.; Yamada, K.; Satoh, H.; Watanabe, M.; Miura, S.; Sakata, S.; Sasaki, T.; Matsuda, A. J. Org. Chem., 1997, 62, 3140-3152.
10. The optimal geometries of four model carbocation intermediates were obtained using AMI methods. The net atom charges were calculated by RHF/6-31G * after geometry optimizations.
11. Folli, U.; Iarossi, D.; Taddei, F. J. Chem. Soc., Perkin Trans. II, 1974, 933-937.
12. 2 had no effects on the Pummerer reaction.
13. The structures of α and β isomers were confirmed by nοe experiments as shown in below after the HPLC separation. (Formula Presented)
14. Although it was thought that introduction of 2,4,6-trimethoxybenzoyl group would be more effective for the reaction, all of attempts to introduce 2,4,6-trimethoxybenzoyl group on both hydroxyl groups were failed due to steric hindrance.