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Michael type addition of DBU (1,8-diazabicyclo[5,4,0]undec-7-ene) phthalimide salt to 4,6-di-O-acetyl-2,3-dideoxy-aldehydo-D-erythro-trans-hex-2-enos e 2 and concomitant acetyl shift give an anomeric mixture of arabino and ribo isomers of 5,6-di-O-acetyl-2,3-dideoxy-3-phthalimido-D-hexofuranose 3 which after acetylation at the anomeric hydroxy group is separated to give 4 and 5. Subsequent reaction with 5'-substituted silylated uracil in the presence of TMS-triflate results in three different 5',6'-di-O-acetyl-2',3'-dideoxy-3'-phthalimido-D-hexofuranose nucleosides 7, 9, and 10 which were deprotected to give the corresponding 3'-amino nucleosides 8, 11, and 12. The compounds 7-12 were investigated for their activity against HSV-1 and HIV-1.
J Lau, and
E B Pedersen, and
L V Jensen, and
C M Nielsen
January 1990,
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J Lau, and
E B Pedersen, and
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C M Nielsen
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Archiv der Pharmazie,
J Lau, and
E B Pedersen, and
L V Jensen, and
C M Nielsen
March 1973,
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J Lau, and
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L V Jensen, and
C M Nielsen
December 1996,
Journal of medicinal chemistry,
J Lau, and
E B Pedersen, and
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C M Nielsen
May 2009,
Nucleosides, nucleotides & nucleic acids,
J Lau, and
E B Pedersen, and
L V Jensen, and
C M Nielsen
November 2004,
Organic letters,
J Lau, and
E B Pedersen, and
L V Jensen, and
C M Nielsen
July 1975,
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J Lau, and
E B Pedersen, and
L V Jensen, and
C M Nielsen
April 2007,
Journal of medicinal chemistry,
J Lau, and
E B Pedersen, and
L V Jensen, and
C M Nielsen
December 2010,
Bioorganic chemistry,
J Lau, and
E B Pedersen, and
L V Jensen, and
C M Nielsen
January 1999,
Nucleosides & nucleotides,
