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Original Articles

Synthesis of 2,2′-Anhydro-1 - (3′ -deoxy -3′ -iodo-β-D-arabino-furanosyl) thymine and Its Derivatives as Versatile Synthetic Intermediates

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Pages 457-471 | Received 30 Aug 1991, Accepted 25 Nov 1991, Published online: 23 Sep 2006

References

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  • Lessor , R. A. and Leonard , N. J. 1981 . J. Org. Chem. , 46 : 4300
  • Norman , D. G. and Reese , C. B. 1983 . Synthesis , 304
  • Robins , M. J. , Wilson , J. S. and Hansske , F. 1983 . J. Am. Chem. Soc. , 105 : 4059
  • Doboszewski , B. , Chu , C. K. and Halbeek , H. V. 1988 . J. Org. Chem. , 53 : 2777
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  • Rosemeyer , H. and Seela , F. 1989 . Helv. Chim. Acta , 72 : 1084
  • Serafinowski , P. 1990 . Synthesis , : 411
  • Sekine , M. and Nakanishi , T. 1990 . J. Org. Chem. , 55 : 924
  • Czernecki , S. and Valéry , J.-M. 1991 . Synthesis , 239
  • Arabinosyl or ribosyl thymine is several tens of times more expensive than thymidine
  • Škarić , V. and Matulić-Adamić , J. 1980 . Helv. Chim. Acta , 63 : 2179 An unsuccessful attempt to convert 1 into a cis-B-glycol by the I2/AgOAc method is described:
  • Horwitz , J. P. , Chua , J. , Da Rooge , M. A. , Noel , M. and Klundt , I. L. 1966 . J. Org. Chem. , 31 : 205
  • Although DMF can also be used, chloroform is recommended in order to avoid decomposition of the product during lengthy evaporation
  • Compound 2 is also rather unstable even in neutral solutions, especially under light, giving 1 as one of the decomposition products
  • Our attempts to crystallize 4a in non-solvated form have been unsuccessful. However, a very recent publication 18 has attributed mp 130–134°C (EtOH) to this compound, while we obtained 4a as a highly crystallizable mono-ethyl acetate solvate (see Experimental Section)
  • Huang , J.-T. , Chen , L.-C. , Wang , L. , Kim , M.-H. , Warshaw , J. A. , Armstrong , D. , Zhu , Q.-Y. , Chou , T.-C. , Watanabe , K. A. , Matulić-Adamić , J. , Su , T.-L. , Fox , J. J. , Polsky , B. , Barton , P. A. , Gold , J. W. M. , Hardy , W. D. and Zuckerman , E. 1991 . J. Med. Chem. , 34 : 1640
  • Webb , T. R. , Mitsuya , H. and Broder , S. 1988 . J. Med. Chem. , 31 : 1475 For the corresponding 5′-0-(4,4′-dimethoxytrityl) derivatives, see:
  • Brown , D. M. , Todd , A. R. and Varadarajan , S. 1957 . J. Chem. Soc. , 868
  • Doerr , I. L. and Fox , J. J. 1967 . J. Org. Chem. , 32 : 1462
  • Doerr , I. L. , Cŭshley , R. J. and Fox , J. J. 1968 . J. Org. Chem. , 33 : 1592
  • Horwitz , J. P. , Chua , J. , Urbanski , J. A. and Noel , M. 1963 . J. Org. Chem. , 28 : 942
  • In our experiments, both 4a and 4b were not crystalline in non-solvated form, the former being a foam and the latter an amorphous powder (The mono-ethyl acetate of 4a is crystalline17). However, msp of non-solvated 4a17,18 and 4b25 are described. Moreover, no convincing information for comparison with our compounds are available from the ill-resolved 1H NMR data18,25 and the erroneous chemical formula of 4a.18
  • JP (Japan Patent) 1–151595: mp of 4b, 144–146°C.
  • Fox , J. J. , Young , N. and Bendich , A. 1957 . J. Am. Chem. Soc. , 79 : 2775
  • Lit18 has attributed mp 128–133°C to 7b and mp 125–130°C to 8a.
  • Sasaki , T. , Minamoto , K. and Kidokoro , N. 1973 . O. P. P. International , 5 ( 2 ) : 75
  • We have encountered other similar results in the reactions of 2 with various nucleophiles

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