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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 2
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Original Articles

Novel Synthesis of 4,5-Trisubstituted Dioxolanes via Methylthiomethyl Ethers

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Pages 111-117 | Received 20 Aug 1979, Published online: 05 Dec 2006

References

  • Corey , E. J. and Bock , M. G. 1975 . Tetrahedron Letters , : 3269
  • Pojer , P. M. and Angyal , S. J. 1976 . Tetrahedron Letters , : 3067 Aust. J. Chem., 31, 1031 (1978)
  • Yamada , K. , Kato , K. , Nagase , H. and Hirata , Y. 1976 . Tetrahedron Letters , : 65
  • Holtan , R. A. and Davis , R. G. 1977 . Tetrahedron Letters , : 533
  • Nagasawa , N. , Kumanshiro , I. and Takenishi , T. 1967 . Bull. Chem. Soc., Japan , 40 : 1732 The synthesis of 1 from PhCH2OCH2CH(OH)CČH(OEt)2 was carried out in eight steps. The details of the synthesis will be described in a forthcoming publication
  • The structures assigned to the compounds reported herein were confirmed by infrared, proton magnetic resonance and mass spectrometric data. NMR spectra were determined on a Varian T-60-A in CDCl3 and gc-ms spectra on a Finigan 1015C. Melting points were taken on a Thomas-Hoover melting point apparatus and are uncorrected
  • Yamada . reference 3, employed cadmium carbonate in place of calcium carbonate for the removal of MTM ethers
  • Karmas , G. and Scheer , I. U. S. Patent . 3,192,202 . June 29, 1965 . I. Scheer, U.S. Patent 3,390,157, June 25, 1968
  • Treatment of anagesterone (6) with DMSO and Ac2O at 90° for 48 hr gave 8 as the only isolable product. Compound 8 is likely formed by acetate displacement on 7 which is initially formed
  • Wheeler , D. M. S. and Wheeler , M. M. 1972 . Organic Reactions in Steroid Chemistry Edited by: Fried , J. and Edwards , J. A. Vol. I , 79 J. C. Grivas, J. Org. Chem., 31, 1349 (1966); L. L. Smith, J. J. Garbarini, J. J. Goodman, M. Marx and M. Mendelsohn, J. Amer. Chem. Soc., 82, 1437 (1960); E. Oliveto and E. B. Hershberg, J. Amer. Chem. Soc., 75, 488 (1953)

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