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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 3
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Original Articles

Synthesis of Morphine-3-Glucuronide

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Pages 231-236 | Received 07 Feb 1975, Published online: 05 Dec 2006

References

  • Woods , L. A. 1954 . J. Pharmacol. Exptl. Therap. , 112 : 158
  • Fujimoto , J. M. and Way , E. L. 1957 . J. Pharmacol. Exptl. Therap. , 121 : 340
  • Scrafoni , J. T. and Clauet , D. H. 1971 . “ Chapter 6 ” . In Narcotic Drugs, Biochemical Pharmacology , Edited by: Clauet , D. H. New York , N. Y. : Plenum Press .
  • Yoshimura , H. , Oguri , K. and Tsukamoto , H. 1968 . Chem. Pharm. Bull. , 16 : 2114
  • Yoshimura , H. , Oguri , K. and Tsukamoto , H. 1968 . Tetrahedron Lett. , : 483
  • Liebman , A. Arnold Dr. Nutley , N. J. : Hoffman-La Roche, Inc. . informed us that they were unable to develop a successful synthesis of 1 using modified Koenigs-Knorr methods or by direct fusion of morphine with methyl tetra-O-acetyl-β-d-glucopyranuronate
  • In each experiment the progress of the reaction and the purity of the products obtained were determined by tic on silica gel plates using chloroform-methanol-water 1:1:0.3 as solvent systems
  • The use of tributylamine in place of sodium hydroxide as the base and substitution of pyridine for acetone-water as the solvent gave other sugar derivatives but no 1 or 4
  • Bollenback , G. N. , Long , J. W. , Benjamin , D. G. and Lindquist , J. A. 1955 . J. Amer. Chem. Soc. , 77 : 3310
  • A brown precipitate was obtained in each case. However, no 1 was obtained on hydrolysis of the solid with lithium hydroxide
  • When the potassium salt was used, the final product was difficult to separate from inorganic potassium salts
  • Newth , F. H. and Philips , G. O. 1953 . J. Chem. Soc , : 2896 The addition of potassium iodide converts 3 to the more reactive iodo sugar. See
  • Hall , L. D. 1964 . Tetrahedron Lett. , : 1457

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