Synthesis of 2/-Deoxy-L-fucopyranosylcarminomycinone and -e-pyrromycinone As Well As 2'-Deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and-e-pyrromycinone
Document Type
Article
Publication Date
1-1-1981
Abstract
Treatment of di-O-acetyl-2-deoxy-L-fucopyranosyl bromide with carminomycinone and e-pyrromycinone in the presence of mercuric bromide and mercuric cyanide afforded 3’,4'-di-0-acetyl-2,-deoxy-L-fucopyranosylcarminomycinone and -e-pyrromycinone. Similarly, when di-O-acetyl-2-deoxy-D-erytrho-pentopyranosyl chloride was treated with daunomycinone, carminomycinone and e-pyrromycinone, the di-O-acetyl derivatives of the anthracyclinone glycosides were obtained. Deacetylation of the previous acetates with sodium methoxide afforded 2'-deoxy-L-fucopyranosylcarminomycinone and -e-pyrromycinone, as well as 2'-deoxy-D-eryhro-pentopyranosyldaunomycinone, -carminomycinone, and -e-pyrromycinone. 2'-Deoxy-L-fucopyranosylcarminomycinone was found to be more active than carminomycin at higher dosages on L1210. © 1981, American Chemical Society. All rights reserved.
Publication Title
Journal of Medicinal Chemistry
Recommended Citation
El Khadem, H.,
&
Swartz, D.
(1981).
Synthesis of 2/-Deoxy-L-fucopyranosylcarminomycinone and -e-pyrromycinone As Well As 2'-Deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and-e-pyrromycinone.
Journal of Medicinal Chemistry,
24(1), 112-115.
http://doi.org/10.1021/jm00133a023
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/8047