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Synthesis 1989; 1989(5): 384-387
DOI: 10.1055/s-1989-27259
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A Convenient Route to 3′-Amino-3′-deoxythymidine

Mohammed S. Motawia* , Jesper Wengel, Ahmed E.-S. Abdel-Megid, Erik B. Pedersen
  • *Department of Chemistry, Odense University, Campusvej 55, DK-5230 Odense M, Denmark
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Publication Date:
17 September 2002 (online)

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Efficient and convenient procedures are reported for the synthesis of the title compound 9 and its α-anomer 10. Thus, the direct condensation of phthalimide with unprotected 2-deoxy-D-ribose (1) using the P4O10/H2O/n-Bu3N reagent in CHCl3 at 40°C followed by acetylation afforded the di-O-acetyl-phthalimido derivatives 2 and 3 which can also be synthesized via reaction of DBU phthalimide salt with 4-acetoxy-5-hydroxy-2-pentenal 5. Reaction of 2 with silylated thymine using the Lewis acid trimethylsilyl triflate as catalyst afforded compounds 7 and 8 which were separated by fractional crystallization, and deprotected by treatment with 33 % methylamine/ethanol to give the corresponding 3-aminonucleosides 9 and 10, respectively.