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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1993
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00218820_v46_n11_p1720_Horton http://hdl.handle.net/20.500.12110/paper_00218820_v46_n11_p1720_Horton |
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paper:paper_00218820_v46_n11_p1720_Horton2025-07-30T17:24:58Z Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine anthracycline derivative daunosamine antineoplastic activity article chemical structure drug synthesis human human cell priority journal 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. 1993 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00218820_v46_n11_p1720_Horton http://hdl.handle.net/20.500.12110/paper_00218820_v46_n11_p1720_Horton |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
anthracycline derivative daunosamine antineoplastic activity article chemical structure drug synthesis human human cell priority journal |
| spellingShingle |
anthracycline derivative daunosamine antineoplastic activity article chemical structure drug synthesis human human cell priority journal Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine |
| topic_facet |
anthracycline derivative daunosamine antineoplastic activity article chemical structure drug synthesis human human cell priority journal |
| description |
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. |
| title |
Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine |
| title_short |
Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine |
| title_full |
Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine |
| title_fullStr |
Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine |
| title_full_unstemmed |
Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine |
| title_sort |
synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine |
| publishDate |
1993 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00218820_v46_n11_p1720_Horton http://hdl.handle.net/20.500.12110/paper_00218820_v46_n11_p1720_Horton |
| _version_ |
1840326317185171456 |