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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 19
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Original Articles

Polymer-Supported Regioselective Synthesis of Methyl 2-O- and 2, 3-Di-O-(4,6-Dimethylpyrimidin-2yl)-α-D-Glucopyranosides

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Pages 3539-3547 | Received 12 Jan 1998, Published online: 22 Aug 2006

REFERENCES

  • Japanese Patent 04,342,573 . 1992 . Mitsubishi Petrochemical Co. Ltd.
  • Schering , A.-G. European Patent 439,243 . 1991 .
  • Schering , A.-G. Federal Republic Germany Patent3,924,260 . 1991 .
  • Fréchet , J. M.J. , Nuyens , L. J. and Seymour , E. 1979 . J. Am. Chem. Soc. , 101 ( 2 ) : 432
  • Thompson , L. A. and Ellman , J. A. 1996 . Chem. Rev. , 96 : 555
  • Farrall , M. J. and Fréchet , J. M.J. 1976 . J. Org. Chem. , 41 ( 24 ) : 3877
  • Li , Z. M. , Liao , Y. , Wang , L. X. and Yang . 1996 . Z. Chemical Research in Chinese Universities (English) , 12 ( 4 ) : 360
  • Stoddart , J. F. 1971 . Stereochemistry of Carbohydrates , 137 John Wiley & Sons, Inc. .
  • Liao , Y. and Li , Z. M. 1996 . Synth. Commun. , 26 ( 9 ) : 1669 Anti-periplanar protons on the pyranoid ring usually exhibit a large value for vicinal coupling constant (7–10 Hz), whereas syn-clinal protons exhibit a small value (1–4 Hz).8 In our case, the proton which was on the same carbon with the pyrimidinyloxo group coupled with its two vicinal protons to give a quartet peak due to one anti-periplanar coupling (3Jaa =9.8 Hz) and another syn-clinal coupling (3Jea =3.7 Hz). In the stable chair conformation of the pyranoid ring which was shown in the scheme, H2 is syn-clinal to H1 anti-periplanar to H3 while H3 is anti-periplanar to both H2 and H4. Obviously, only the structure of 2-O substituted product 6 can accord with the 1H NMR result. Furthermore, 1H NMR result of 2,3-di-O-substituted product 7 (H 2: 5.32ppm, dd, 3J12=3.7Hz; 3J23=9.3Hz; H 3: 5.47ppm, t, 3J23=3J34=9.3Hz) also supported the above conclusion

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