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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 19
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Original Articles

A Refined Method for the Removal of the Methoxymethyl (MOM) Protecting Group for Carbinols with Acidic Ion-Exchange Resin

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Pages 2823-2828 | Accepted 23 May 1992, Published online: 23 Sep 2006

References

  • Greene , T. W. 1981 . Protective Groups in Organic Syntheses , 16 New York : John Wiley and Sons, Inc. . and references cited therein
  • Grove , J. F. , MacMillan , J. , Mulholland , T. P.C. and Turner , W. B. 1961 . J. Chem. Soc. , : 3049
  • Murofushi , N. , Iriuchijima , S. , Takahashi , N. , Tamura , S. , Kato , J. , Wada , Y. , Watanabe , E. and Aoyama , T. 1966 . Agri. Biol. Chem. , 30 : 317
  • Mander , L. N. 1988 . Nat. Prod. Rep. , 5 : 541
  • Hanessian , H. , Delorme , D. and Dufresme , Y. 1984 . Tetrahedron Lett. , : 2515
  • Guindon , Y. , Yoakim , C. and Morton , H. E. 1984 . J. Org. Chem. , 49 : 3912
  • Shimano , M. , Nagaoka , H. and Yamada , Y. 1990 . Chem. Pharm. Bull. , 38 : 276
  • This kind of acidic ion-exchange resin, Amberlyst H-15 or Dowex-50W-X8, was already used as a catalyst for protection of alcohols with the tetrahydropyranyl group and its removal at room temperature. 7
  • Bongini , A. , Gardillo , G. , Orena , M. and Sandri , S. 1979 . Synthesis , : 618
  • Beier , R. and Mundy , B. P. 1979 . Synth. Commun. , 9 : 271
  • Kieczykowsky , G. R. , Quesada , M. L. and Schlessinger , R. H. 1982 . J. Am. Chem. Soc. , 102 : 782
  • Kametani , T. , Katoh , T. , Tsubuki , M. and Honda , T. 1986 . J. Am. Chem. Soc. , 108 : 7055
  • Purchased resin, Dowex-50W-X2 (H +form) was used after successive washing with dist. H2O, 2N NaOH, dist. H2O and 2N HCl, then dist. H2O on a glass-filter until the filtrate was neutral. Without this conditioning, the reactions were complicated by side-reactions resulted from strongly acidic conditions (see text)

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