Download PDF
Synthesis 1989; 1989(5): 384-387
DOI: 10.1055/s-1989-27259
communication
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.

      >