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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/4417501
- author
- Ohlin, Markus
LU
; Manner, Sophie
LU
; Lofgren, Johanna
; Persson, Andrea
LU
and Ellervik, Ulf
LU
- organization
- publishing date
- 2014
- 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
- 2016-04-01 14:56:24
- date last changed
- 2025-04-04 14:26:36
@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}},
doi = {{10.1039/c4ra01056f}},
volume = {{4}},
year = {{2014}},
}