In:
Chemistry – An Asian Journal, Wiley, Vol. 4, No. 7 ( 2009-07-06), p. 1114-1125
Abstract:
Sweets for my sweet ! Efficient synthesis of the deoxysugar part of versipelostatin (VST) was achieved by direct and stereoselective glycosidation of the reduced VST aglycon. Comparison of the synthetic and natural VST products using NMR indicate that VST has a β‐d‐digitoxose‐(1,4)‐α‐l‐oleandrose‐(1,4)‐β‐d‐digitoxose trisaccharide. A biological assay indicates that the deoxyoligosaccharide unit of the synthetic glycoside is important for biological activity. magnified image Efficient synthesis of the deoxysugar part of versipelostatin (VST) was achieved by direct and stereoselective glycosylation of the reduced VST aglycon. Activation of 2‐deoxyglycosyl imidate with IBr under basic conditions enables α‐selective glycosylation of β‐2‐deoxylglycosides without anomerization. Comparison of the synthetic and natural VST products using NMR indicates that versipelostatin has a β‐ D ‐digitoxose‐(1,4)‐α‐ L ‐oleandrose‐(1,4)‐β‐ D ‐digitoxose trisaccharide. In addition, results of a biological assay indicate that the deoxyoligosaccharide unit of the synthetic glycoside was important for biological activity of the compound.
Type of Medium:
Online Resource
ISSN:
1861-4728
,
1861-471X
DOI:
10.1002/asia.200800448
Language:
English
Publisher:
Wiley
Publication Date:
2009
detail.hit.zdb_id:
2233006-9
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