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Synthesis 1993; 1993(8): 790-792
DOI: 10.1055/s-1993-25943
short paper
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2,3,6-Trideoxy-5-O-(4-nitrobenzoyl)-3-trifluoroacetamido-L-ribo-hexofuranosyl Bromide - A Suitable Furanoid Ristosamine Glycosylation Reagent

Krzysztof Walczak* , Jesper Lau, Erik B. Pedersen
  • *Department of Chemistry, Odense University, Campusvej 55, DK-5230 Odense M, Denmark
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Publication Date:
27 September 2002 (online)

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5-O-Acetyl-2,3,6-trideoxy-3-phthalimido-ß-L-ribo-hexofuranose (2) was converted to its corresponding methyl glycoside 3. After deprotection with 33% methylamine in ethanol and subsequent protection of the amino group with trifluoroacetic anhydride and the hydroxy group with 4-nitrobenzoyl chloride, the resulting compound 5 was transformed into the appropriate glycosyl bromide 7 via the 1-O-acetyl derivative 6. Compound 7 was coupled with daunomycinone in the presence of yellow mercury(II) oxide and mercury(II) bromide.

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