Uridine 5'-monoselenoacetals as substrates for diastereoselective homolytic C-C bond formation

Tetrahedron

Volumn 52, Issue 28, 1996, Pages 9469-9484

  Haraguchi, Kazuhiro ^a   Tanaka, Hiromichi ^a   Saito, Shigeru ^a   Kinoshima, Satomi ^a   Hosoe, Motoi ^a   Kanmuri, Kazuhiro ^a   Yamaguchi, Kentaro ^a   Miyasaka, Tadashi ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

C C bond formation; diastereoselectivity; monoselenoacetal; radical reaction; zuridine

Indexed keywords

ACETAL DERIVATIVE;

ARTICLE; COVALENT BOND; DIASTEREOISOMER; MOLECULAR INTERACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030575402     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00483-8     Document Type: Article

References (29)

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15. 11) For ease of comparison with ordinary nucleosides, the trivial 6,5′-cyclo designation with conventional nucleoside ring numbering is used in this article.
16. 12) The atomic coordinates for 12, 15, 20, and 27 are available on request from the Cambridge Crystallographic Data Centre, University of Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK.
17. 13) Another evidence of the depicted stereochemistry of 13 came from an NOE enhancement observed between H-6 and H-2′ (5.9%).
18. 5,6= 3.3 Hz.
19. 15) For a review concerning the gauche effect: Wolfe, S. Acc. Chem. Res. 1972, 5, 102-111.
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22. 18) The present strategy has recently been applied to the synthesis of 5′-C-deuterium-labelled 2′-deoxyribo-nucleosides: Kawashima, E.; Toyama, K.; Ohshima, K.; Kainosho, M.; Kyogoku, Y.; Ishido, Y. Tetrahedron Lett. 1995, 36, 6699-6700.
23. 2), 3.0% (H-5′ vs. 5-Me), 11.2% (H-6 vs. H-3′).
24. 20) Compound 27 (mp 172-174 °C, acetone-hexane) used for X-ray crystallographic analysis was obtained from 29 by desilylation followed by acetylation.
25. 21) The stereochemistry of 29 and 31 was confirmed by conversion to 27.
26. 22) Huval, C. C.; Singleton, D. A. Tetrahedron Lett. 1993, 34, 3041-3042.
27. 23) It is also conceivable that a buttressing effect of the 2′-O-protecting group to the 3′-position is working as an additional factor to increase the steric encumberment.
28. 24) The 3′-endo sugar pucker of 27 was evident from its X-ray analysis.
29. 25) Compound 33 was prepared by oxidation of 2′,3′-bis-O-(tert-butyldimethylsilyl)uridine according to the published procedure: Camarasa, M-J.; De las Heras, F. G.; Pérez-Pérez, M. J. Nucleosides Nucleotides 1990, 9, 533-546.