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Titolo:
HYDROXYMETHYL-ALPHA-L-THREO-PENTOFURANOSYL)URACILS
Autore:
HREBABECKY H; BUDESINSKY M; MASOJIDKOVA M; HAVLAS Z; HOLY A;
Indirizzi:
ACAD SCI CZECH REPUBL,INST ORGAN CHEM & BIOCHEM,FLEMINGOVO NAM 2 CR-16610 PRAGUE 6 CZECH REPUBLIC
Titolo Testata:
Collection of Czechoslovak Chemical Communications
fascicolo: 6, volume: 62, anno: 1997,
pagine: 957 - 970
SICI:
0010-0765(1997)62:6<957:H>2.0.ZU;2-L
Fonte:
ISI
Lingua:
ENG
Soggetto:
MOLECULAR-ORBITAL METHODS; NMR COUPLING-CONSTANTS; GAUSSIAN-TYPE BASIS; CONFORMATIONAL-ANALYSIS; SUGAR RING; SUBSTITUENT ELECTRONEGATIVITIES; ORGANIC-MOLECULES; KARPLUS EQUATION; NUCLEOSIDES; NUCLEOTIDES;
Keywords:
4'-C-HYDROXYMETHYLURIDINE; ALKYLIDENE DERIVATIVES; CONFORMATIONAL ANALYSIS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
25
Recensione:
Indirizzi per estratti:
Citazione:
H. Hrebabecky et al., "HYDROXYMETHYL-ALPHA-L-THREO-PENTOFURANOSYL)URACILS", Collection of Czechoslovak Chemical Communications, 62(6), 1997, pp. 957-970

Abstract

ene-4-C-hydroxymethyl-alpha-L-lyxofuranosyl)uracil (I) was converted in seven steps into -hydroxymethyl-alpha-L-threo-pentofuranosyl)uracil(8) and further into isoprapylidene-alpha-L-threo-pentofuranosyl)uracil (9). Successive benzoylation, removal of the isopropylidene group, reaction with acetaldehyde diethyl acetal, and debenzoylation afforded(R)- and -hydroxymethyl-alpha-L-threo-pentofuranosyl)uracil (10a and 10b, respectively). Reaction of ethyloxymethyl-alpha-L-threo-pentofuranosyl)uracil (14) with dichloromethane under conditions of phase transfer, followed by detritylation, afforded -O-methylidene-alpha-L-threo-pentofuranosyl)uracil (15). Compound 14 was obtained from the derivative 8 by partial silylation, tritylation and desilylation. The absoluteconfiguration of the isomeric ethylidene derivatives 10a and 10b was determined by NMR spectroscopy and the population of the deoxypentofuranose ring conformers was derived from the vicinal coupling constants I(H,H). The obtained results were compared with energy calculations. Neither of the prepared nucleoside analogues was active in vitro against HIV-I and HIV-2.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 16/07/20 alle ore 19:09:33