Details
| Original language | English |
|---|---|
| Pages (from-to) | 2397-2403 |
| Number of pages | 7 |
| Journal | Synthesis |
| Issue number | 14 |
| Publication status | Published - 28 Jun 2006 |
Abstract
The first synthesis of the trisaccharide unit of versipelostatin, a down regulator of grp78, was achieved, utilizing methyl triflate promoted glycosidations of thioethyl glycosyl donors of D-digitoxose and D-cymarose with protected digitoxal. The synthesis was terminated by the preparation of a thioglycoside based on diethyldithionophosphonic acid which is ready for further glycosidations with aglycons. Comparison of NMR spectroscopic data of two trisaccharides with the data reported for versipelostatin supported the configuration of the monosaccharide units as well as glycosidic linkages.
Keywords
- Antibiotics, Deoxy sugars, Glycoconjugates, Glycols, Glycosidations, Thioglycosides
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Synthesis, No. 14, 28.06.2006, p. 2397-2403.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Total synthesis of the trisaccharide unit of the molecular chaperone down-regulator versipelostatin
AU - Kunst, Eike
AU - Kirschning, Andreas
PY - 2006/6/28
Y1 - 2006/6/28
N2 - The first synthesis of the trisaccharide unit of versipelostatin, a down regulator of grp78, was achieved, utilizing methyl triflate promoted glycosidations of thioethyl glycosyl donors of D-digitoxose and D-cymarose with protected digitoxal. The synthesis was terminated by the preparation of a thioglycoside based on diethyldithionophosphonic acid which is ready for further glycosidations with aglycons. Comparison of NMR spectroscopic data of two trisaccharides with the data reported for versipelostatin supported the configuration of the monosaccharide units as well as glycosidic linkages.
AB - The first synthesis of the trisaccharide unit of versipelostatin, a down regulator of grp78, was achieved, utilizing methyl triflate promoted glycosidations of thioethyl glycosyl donors of D-digitoxose and D-cymarose with protected digitoxal. The synthesis was terminated by the preparation of a thioglycoside based on diethyldithionophosphonic acid which is ready for further glycosidations with aglycons. Comparison of NMR spectroscopic data of two trisaccharides with the data reported for versipelostatin supported the configuration of the monosaccharide units as well as glycosidic linkages.
KW - Antibiotics
KW - Deoxy sugars
KW - Glycoconjugates
KW - Glycols
KW - Glycosidations
KW - Thioglycosides
UR - http://www.scopus.com/inward/record.url?scp=33746622920&partnerID=8YFLogxK
U2 - 10.1055/s-2006-942450
DO - 10.1055/s-2006-942450
M3 - Article
AN - SCOPUS:33746622920
SP - 2397
EP - 2403
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 14
ER -