Sophie Manner
Director of studies
Short and efficient synthesis of a daunosamine donor from L-fucal
Author
Summary, in English
Anthracyclines, e. g. daunorubicin, doxorubicin, and idarubicin, consist of a tetracycline moiety linked via a glycosidic bond to a sugar residue, usually the aminosugar daunosamine. The anthracyclines are efficient chemotherapeutic agents against cancer, but their use is limited due to cardiotoxicity and induction of multidrug resistance. In the search for new anthracycline analogs, a daunosamine donor that can be used to glycosylate suitable aglycons is of utmost importance. Here, we present a short and efficient synthesis of the versatile donor p-tolyl 4-O-acetyl-3-azido-2,3,6-trideoxy-1-thio-alpha-L-lyxo-hexopyranoside in 3 steps from commercially available L-fucal with an overall yield of 32%. The same procedure can be used to synthesize the donor p-tolyl 4-O-acetyl-3-azido-2,3,6-trideoxy-1-thio-alpha-L-arabino-hexopyranoside in 28% overall yield from L-rhamnal, for the synthesis of epirubicin analogs.
Department/s
- Centre for Analysis and Synthesis
- Glycobiology
Publishing year
2014
Language
English
Pages
12486-12489
Publication/Series
RSC Advances
Volume
4
Issue
24
Document type
Journal article
Publisher
Royal Society of Chemistry
Topic
- Chemical Sciences
Status
Published
Research group
- Glycobiology
ISBN/ISSN/Other
- ISSN: 2046-2069