Synthesis of antiviral nucleosides from crotonaldehyde. Part 3.1,2 total synthesis of didehydrodideoxythymidine (d4T)
摘要:
The total synthesis of the antiviral agent d4T 3 from the epoxyalcohol 2, itself derived from crotonaldehyde 1, in 6 steps and 18% overall yield is described.
In this study we report on the characterization of a series of pentacoordinate aluminum 8-hydroxyquinolines, AlQ(2)X (X = F, Cl, Br), composed of two 8-hydroxyquinoline (8-HQ) groups and one halogen ligand. These were prepared by reacting 8-hydroxyquinoline and dialkylaluminum halide stoichiometrically. The lambda(max)s of absorption and emission were in the range of 385-388 and 515-516 nm, respectively, which were similar to AlQ(3). The molar absorptivity of AlQ(2)X is similar regardless of the X group but emission efficiency of AlQ(2)X is 2-3 fold higher than that of AlQ(3) when X = F or Br, but not when X = Cl. This result can be attributed to decreased quenching of energy due to a less steric environment by reducing quinolinate content. The overall molecular orbital structures and the absorption spectra of AlQ(2)X and AlQ(3) are very similar due to a single quinolinate unit. The value of the potential difference of AlQ(2)Xs between anodic and cathodic waves (Delta E = 3.12 V) is close to the estimated HOMO-LUMO energy gap (the optical band gap, Delta E-optical similar to 1240/lambda(max)), 3.19 eV. Detailed optical and electrochemical properties of AlQ(2)X are discussed. (C) 2011 Elsevier B. V. All rights reserved.
Effect of the nature of the organoaluminum compound on the direction of the reaction with xenon difluoride
作者:R. G. Bulgakov、V. N. Yakovlev、G. Ya. Maistrenko、G. A. Tolstikov、V. P. Kazakov
DOI:10.1007/bf00952953
日期:1986.2
BULGAKOV, R. G.;YAKOVLEV, V. I.;MAJSTRENKO, G. YA.;TOLSTIKOV, G. A.;KAZAK+, IZV. AN CCCP. CEP. XIM., 1986, N 2, 490-491
作者:BULGAKOV, R. G.、YAKOVLEV, V. I.、MAJSTRENKO, G. YA.、TOLSTIKOV, G. A.、KAZAK+
DOI:——
日期:——
Process for the synthesis of 2',3'-dideoxynucleosides
申请人:The Regents of the University of California
公开号:US05220003A1
公开(公告)日:1993-06-15
Ziegler; Koester, Justus Liebigs Annalen der Chemie, 1957, vol. 608, p. 1,6