2'-DEOXYPUROMYCIN - SYNTHESIS AND ANTIVIRAL EVALUATION

A new synthesis of 2'-deoxypuromycin (18) as well as its alpha-anomer 17 is described. Reaction of 1,5-di-O-acetyl-2,3-dideoxy-3-phthalimide-beta-D-erythro-pentofuranose (3) with silylated 6-dimethylaminopurine using trimethylsilyl trifIuoromethanesulfonate as catalyst afforded the alpha and be...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 3; pp. 265 - 270
Main Authors MOTAWIA, MS, MELDAL, M, SOFAN, M, STEIN, P, PEDERSEN, EB, NIELSEN, C
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.03.1995
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
2'-DEOXY, 3'-PHTHALIMIDO
HIV-1
NUCLEOSIDES
2'-DEOXYPUROMYCIN
ADENOSINE
3'-AMINO-2',3'-DEOXY-N-6,N-6-DIMETHYL
NUCLEOSIDE SYNTHESIS
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Summary:A new synthesis of 2'-deoxypuromycin (18) as well as its alpha-anomer 17 is described. Reaction of 1,5-di-O-acetyl-2,3-dideoxy-3-phthalimide-beta-D-erythro-pentofuranose (3) with silylated 6-dimethylaminopurine using trimethylsilyl trifIuoromethanesulfonate as catalyst afforded the alpha and beta nucleosides 7 and 12 in 15 and 25% yield, respectively. After deblocking of both amino and hydroxy groups with methylamine in ethanol, the nucleosides were condensed with Fmoc-4-O-methyl-L-tyrosine and subsequently deprotected to give the target compounds 17 and 18. Compound 3 is converted into its glycosyl bromide 4 in quantitative yield on treatment with trimethylsilyl bromide, and reacted with the sodium salt of 6-dimethylaminopurine to give the corresponding protected N-7 and N-9 alpha glycosyl nucleosides 7 and 8 in 34 and 39% yield, respectively. The 2'-deoxypuromycin is inactive against HIV-1 in MT-4 cells.
ISSN:0039-7881
DOI:10.1055/s-1995-3892