Synthesis of the Oligosaccharide Moieties of Musettamycin, Marcellomycin and Aclacinomycin A, Antitumor Antibiotics
- 1 May 1988
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 7 (2) , 417-434
- https://doi.org/10.1080/07328308808058934
Abstract
Condensation of benzyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (5) with 4-O-acetyl-3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl bromide (10) carried out under Koenigs-Knorr conditions gave 12. Total deprotection of 12 and N-dimethylation at C-3 led to 17 while selective removal of the 4-O-acetyl group led to 13, a synthetic intermediate for preparing 24 and 33. Condensation of 13 with di-O-acetyl-L-fucal (18) or 4-O-acetyl-L-amicetal (25) in the presence of N-iodosuccinimide followed by hydrogenolysis of the C-2-I bond gave 20 and 27 respectively. The trisaccharide 24 then was obtained from 20 by the same sequence of reactions used to convert 12 into 17. After deacetylation and oxidation, this set of reactions also transformed 27 into 33.This publication has 18 references indexed in Scilit:
- Regioselective Alkylation and Acylation of Methyl, 2,6-Dideoxyhexo-Pyranosides Via Their Stannylene Acetals: Key Step for the Synthesis of Daunosamine and Related Amino-SugarsJournal of Carbohydrate Chemistry, 1987
- Desorption chemical ionization mass spectrometry of anthracyclines and of trisaccharides related to aclacinomycin a and marcellomycinJournal of Mass Spectrometry, 1986
- Synthèse de disaccharides naturels, fragments d'anthracyclines oligosaccharidiquesCarbohydrate Research, 1983
- Synthesis of a trisaccharide related to the antitumour antibiotic, aclacinomycin AJournal of the Chemical Society, Chemical Communications, 1983
- Synthesis of methyl 2,3,6-trideoxy-4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-3-(trifluoroacetamido)-β-L-lyxo-hexopyranosideCarbohydrate Research, 1981
- Darstellung der terminalen Pentadesoxydisaccharideinheit C-B von Anthracyclin‐AntibioticaEuropean Journal of Inorganic Chemistry, 1980
- Synthesen mit 2,6‐Didesoxyglyosylhalogeniden. Aufbau des B – A‐Disaccharid‐Glycosids aus Chromomycin A3European Journal of Inorganic Chemistry, 1980
- Antitumor agents from the bohemic acid complex. 4. Structures of rudolphomycin, mimimycin, collinemycin, and alcindoromycinJournal of the American Chemical Society, 1979
- Synthese α-verknüpfter 2′-Deoxy-2′-iododisaccharideSynthesis, 1978
- Mass spectrometry of some N-acyldaunosamine derivativesCarbohydrate Research, 1974