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

Ohlin, Markus LU ; Manner, Sophie LU ; Lofgren, Johanna; Persson, Andrea LU and Ellervik, Ulf LU (2014) In RSC Advances 4(24). p.12486-12489
Abstract
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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
RSC Advances
volume
4
issue
24
pages
12486 - 12489
publisher
Royal Society of Chemistry
external identifiers
  • wos:000332473400052
  • scopus:84897715118
ISSN
2046-2069
DOI
10.1039/c4ra01056f
language
English
LU publication?
yes
id
4e89291a-3527-4097-9fdd-354f2ddd3833 (old id 4417501)
date added to LUP
2014-04-29 09:05:43
date last changed
2017-01-01 06:30:59
@article{4e89291a-3527-4097-9fdd-354f2ddd3833,
  abstract     = {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.},
  author       = {Ohlin, Markus and Manner, Sophie and Lofgren, Johanna and Persson, Andrea and Ellervik, Ulf},
  issn         = {2046-2069},
  language     = {eng},
  number       = {24},
  pages        = {12486--12489},
  publisher    = {Royal Society of Chemistry},
  series       = {RSC Advances},
  title        = {Short and efficient synthesis of a daunosamine donor from L-fucal},
  url          = {http://dx.doi.org/10.1039/c4ra01056f},
  volume       = {4},
  year         = {2014},
}