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Short and efficient synthesis of a daunosamine donor from L-fucal

In English

Författare

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.

Publiceringsår

2014

Språk

Engelska

Sidor

12486-12489

Publikation/Tidskrift/Serie

RSC Advances

Volym

4

Issue

24

Dokumenttyp

Artikel i tidskrift

Förlag

Royal Society of Chemistry

Ämne

  • Chemical Sciences

Status

Published

Forskningsgrupp

  • Glycobiology

ISBN/ISSN/Övrigt

  • ISSN: 2046-2069