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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 14
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Original Articles

Synthesis of 9-((1,3-Dihydroxy-2-Propoxy)Methyl)Guanine (Dhpg) Via Condensation Of N2sp>u>9-Diacetylguanine With A Sulfinylmethyl Ether

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Pages 1651-1660 | Published online: 03 Jan 2007

References

  • Contribution No. 277 from the Institute of Bio-Organic Chemistry.
  • Present address: The Wellcome Research Laboratories, 3030 Cornwallis Road, Research Triangle Park, NC 27709.
  • Present address: Bristol-Myers Co., Pharmaceutical Research and Development Division, Wallingford, CT 06492-7660.
  • Chachoua , A. , Dieterich , D. , Krasinski , K , Wernz , J. and Buhles , W . 1987 . Ann.of Int. Med. , 107 : 133 Collaborative DHPG Treatment Study Group, N. Eng. J. Med. 1986, 314, 801
  • Martin , J. C. , Matthews , T. R. and Verheyden , J. P.H . 1983 . Vol. 26 , 759 Field, A.K.; Davies, M.E.; Dewitt, C.; Perry, H.C.; Liou, R.; Germershausen, J.; Karkas, J.D.; Ashton, W.T.; Johnston, D.B.R.; Tolman, R.L. Proc. Natl. Acad. Sci. USA 1983, 80, 4139. Schaeffer, H.J. in “Nucleosides, Nucleotides and Their Biological Applications,” Rideout, J. L.; Henry, D.W.; Beacham, L.M., Eds., Academic Press, New York, 1983, pp. 1–17. Ogilvie, K.K.; Cheriyan, U.O.; Radatus, B.K.; Smith, K.O.; Galloway, K.S.; Kennel1, W.L. Can. J. Chem. 1982, 60, 3005 Dvorak C.A.; J Med. Chem.
  • Stewart , A. O. and Williams , R. M. 1985 . J. Amer. Chem. Soc. , 107 : 4289 Nicolaou, K.C.; Seitz, S.P.; Papahatjis, D.P. J. Amer. Chem. Soc. 1983, 105, 2430, and references cited therein
  • Ogilvie , K. K. , Nguyen-ba , N. and Hamilton , R. G. 1984 . Can. J. Chem. , 62 : 1622
  • Schwindeman , J. A. and Magnus , P. D. Tetrahedron Lett. , 1981 4925 Pojer, P.M.; Angyal, S.J. Tetrahedron Lett. 1976, 3067.
  • Quantities of 8 (retention time = 11 min) and 9 (retention time = 13 min) were determined on an Ultrasphere Octyl 5 micron 4.6x150 mm column eluting with 55:45 Methanol/0.005 M NH4PO4H2 at pH 2.5. We thank Linda Foster and Dr. Robert Bergstrom for this analytical work.

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