Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine
Daunosamine, as its 4-O-acetyl-3-N-trinfluoroacetyl glycosyl chloride derivative (1b), has been coupled α-L-glycosidically to the 3- and 4-mono-O-acetyl derivatives of L-rhamnal to afford disaccharide glycal derivatives, whose conversion into the corresponding 2-deoxyglycosides by sequential alkoxyi...
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| Autores principales: | , , , |
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| Formato: | JOUR |
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00218820_v46_n11_p1720_Horton |
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| Sumario: | Daunosamine, as its 4-O-acetyl-3-N-trinfluoroacetyl glycosyl chloride derivative (1b), has been coupled α-L-glycosidically to the 3- and 4-mono-O-acetyl derivatives of L-rhamnal to afford disaccharide glycal derivatives, whose conversion into the corresponding 2-deoxyglycosides by sequential alkoxyiodination-tributylstannane reduction has been evaluated. The sequence sucssfully demonstrated with the methyl glycosides was successfully extended with daunomycinone as the aglycon, providing a preparative route to 7-O-[3-O-(3-amino-2, 3, 6-trideoxy-α-L-lyxohexopyranosyl)-2, 6-dideoxy-α-L-arabino-hexopyranosyl]daunomycinone hydrochloride (15), an analogue of natural anthracycline antibiotics containing daunosamine and a 2, 6-dideoxy-L-hexose. © 1993, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved. |
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