No.141,142
A Valuable Synthetic Intermediate
| A2054 | 2-Amino-6-chloropurine Riboside (1) |
1g 5g |
2-Amino-6-chloropurine riboside (1) is a valuable synthetic intermediate for the preparation of a number of important purine nucleoside derivatives. For example, 6-thioguanosine 2 and 6-selenoguanosine 3 were prepared from a reaction of 1 and the corresponding sodium thiosulfate or potassium selenosulfate.1) 18O-labeled guanosine 4 was incubated from 1 with adenosine deaminase in (18O)-water.2) 2-Amino-6-ethoxypurine riboside 5 and 2-amino-N6-amino-N6-methyladenosine 6 were prepared by treatment of 1 with nucleophiles, sodium ethoxide and methylhydrazine, respectively.3,4) 2-Amino-N6-substituted purine analogues, as typified by 6, were reported as anti-malarial active compounds.4)
References
1) Synthesis of 6-thio- and 6-selenoguanosines
A. J. Jankowski, D. S. Wise, Jr., L. B. Townsend, Nucleosides Nucleotides 1989, 8, 339[DOI].
2) Enzymatic synthesis of [6-18O]gluanosine
a) S. Rayat, P. Majumdar, P. Tipton, R. Glaser, J. Am. Chem. Soc. 2004, 126, 9960[DOI]. b) I. C. M. Kwan, X. Mo, G. Wu, J. Am. Chem. Soc. 2007, 129, 2398[DOI].
3) Synthesis of 6-substituted purines
M. J. Robins, J. S. Wilson, D. Madej, D. L. J. Tyrrell, W. P. Gati, R. J. Lindmark, S. F. Wnuk, J. Heterocyclic Chem. 2001, 38, 1297[DOI].
4) Synthesis of N6-modified purine analogues and there anti-malarial activity
K. Too, D. M. Brown, E. Bongard, V. Yardley, L. Vivas, D. Loakes, Bioorg. Med. Chem. 2007, 15, 5551[DOI].
A. J. Jankowski, D. S. Wise, Jr., L. B. Townsend, Nucleosides Nucleotides 1989, 8, 339[DOI].
2) Enzymatic synthesis of [6-18O]gluanosine
a) S. Rayat, P. Majumdar, P. Tipton, R. Glaser, J. Am. Chem. Soc. 2004, 126, 9960[DOI]. b) I. C. M. Kwan, X. Mo, G. Wu, J. Am. Chem. Soc. 2007, 129, 2398[DOI].
3) Synthesis of 6-substituted purines
M. J. Robins, J. S. Wilson, D. Madej, D. L. J. Tyrrell, W. P. Gati, R. J. Lindmark, S. F. Wnuk, J. Heterocyclic Chem. 2001, 38, 1297[DOI].
4) Synthesis of N6-modified purine analogues and there anti-malarial activity
K. Too, D. M. Brown, E. Bongard, V. Yardley, L. Vivas, D. Loakes, Bioorg. Med. Chem. 2007, 15, 5551[DOI].
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