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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 11
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Original Articles

Regiocontrolled C-8 Acylation of Castanospermine

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Pages 2213-2221 | Received 15 Dec 1995, Published online: 21 Aug 2006

References and Notes

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  • Elbein , A. D. 1984 . CRC Critical Reviews in Biochemistry , 16 : 21
  • Ostrander , G. K. , Scribner , N. K. and Rohrschneider , L. R. 1988 . Cancer Res. , 48 : 1091 and relevant references cited therein
  • Sunkara , P. S. , Bowlin , T. L. , Liu , P. S. and Sjoerdsma , A. 1987 . Biochem. Biophys. Res. Commun. , 148 : 206
  • Gruters , R. A. , Neefjes , J. J. , Tersmette , M. , de Goede , R. E. Y. , Tulp , A. , Huisman , H. G. , Miedema , F. and Ploegh , H. L. 1987 . Nature , 330 : 74
  • Tyms , A. S. , Berrie , E. M. , Ryder , T. A. , Nash , R. J. , Hegarty , M. P. , Taylor , D. L. , Mobberley , M. A. , Davis , J. M. , Bell , E. A. , Jeffries , D. J. , Taylor-Robinson , D. and Fellows , L. E. 1987 . Lancet , ii : 1025
  • Rhinehart , B. L. , Robinson , K. M. , Payne , A. J. , Wheatley , M. E. , Fisher , J. L. , Liu , P. S. and Cheng , W. 1987 . Life Sci. , 41 : 2325
  • Burgess , K. and Henderson , I. 1992 . Tetrahedron , 48 : 4045 and relevant references cited therein
  • Margolin , A. L. , Delnick , D. L. and Whalon , M. R. 1990 . J. Am. Chem. Soc. , 112 : 2849
  • Liu , P. S. , Hoekstra , W. J. and King , C.-H. R. 1990 . Tetrahedron Lett. , 31 : 2829
  • Furneaux , R. H. , Gainsford , G. J. , Mason , J. M. and Tyler , P. C. 1994 . Tetrahedron , 50 : 2131
  • King , C.-H. R. and Ashton , L. unpublished results
  • Tyler , P. C. , Furneaux , R. H. and Mason , J. M. 1994 . Tetrahedron Lett. , 35 : 3143
  • Compound 7 was prepared from 1,8-O-isopropylidenylcastanospermine8 by treatment with CbzCl/DMAP/Et3N in CH2Cl2 at 25 °C. For 7: 1H NMR (CDCl3) δ 7.32 (m, 10 H), 5.15 (d, J = 7.5 Hz, 2 H), 5.10 (d, J = 6.0 Hz, 2 H), 4.95 (m, 2 H), 4.51 (m, 1 H), 3.85 (t, J = 9.0 Hz, 1 H), 3.37 (m, 1 H), 3.06 (m, 1 H), 2.96 (m, 2 H), 2.83 (m, 1 H), 2.20 (m, 1 H), 1.91 (m, 1 H), 1.35 (s, 3 H), 1.16 (s, 3 H); 13C NMR (CDCl3) δ 154.4, 154.2, 135.2, 134.9, 128.6, 128.5, 128.4, 128.3, 128.2, 128.0, 101.2, 78.5, 72.7, 71.1, 69.9, 69.6, 64.2, 62.8, 49.5, 49.3, 33.0, 27.5, 24.8; MS (Cl, NH3) m/z (rel. intensity) 498 (M + H+, 100%), 468 (9), 440 (5), 345 (8).

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