hrcak mascot   Srce   HID

Izvorni znanstveni članak

Synthesis and Intramolecular Rearrangement of Enantiomeric Amino-alcohols in the Aliphatic Thymidine Analogues Series

Vinko Škarić ; Laboratory of Stereochemistry and Natural Products, »Ruđer Bošković" Institute, 41001 Zagreb, Croatia, Yugoslavia
Zlata Raza ; Laboratory of Stereochemistry and Natural Products, »Ruđer Bošković" Institute, 41001 Zagreb, Croatia, Yugoslavia
Biserka Kašnar ; Laboratory of Stereochemistry and Natural Products, »Ruđer Bošković" Institute, 41001 Zagreb, Croatia, Yugoslavia

Puni tekst: engleski, pdf (5 MB) str. 297-306 preuzimanja: 103* citiraj
APA 6th Edition
Škarić, V., Raza, Z. i Kašnar, B. (1986). Synthesis and Intramolecular Rearrangement of Enantiomeric Amino-alcohols in the Aliphatic Thymidine Analogues Series. Croatica Chemica Acta, 59 (1), 297-306. Preuzeto s https://hrcak.srce.hr/177594
MLA 8th Edition
Škarić, Vinko, et al. "Synthesis and Intramolecular Rearrangement of Enantiomeric Amino-alcohols in the Aliphatic Thymidine Analogues Series." Croatica Chemica Acta, vol. 59, br. 1, 1986, str. 297-306. https://hrcak.srce.hr/177594. Citirano 24.06.2021.
Chicago 17th Edition
Škarić, Vinko, Zlata Raza i Biserka Kašnar. "Synthesis and Intramolecular Rearrangement of Enantiomeric Amino-alcohols in the Aliphatic Thymidine Analogues Series." Croatica Chemica Acta 59, br. 1 (1986): 297-306. https://hrcak.srce.hr/177594
Harvard
Škarić, V., Raza, Z., i Kašnar, B. (1986). 'Synthesis and Intramolecular Rearrangement of Enantiomeric Amino-alcohols in the Aliphatic Thymidine Analogues Series', Croatica Chemica Acta, 59(1), str. 297-306. Preuzeto s: https://hrcak.srce.hr/177594 (Datum pristupa: 24.06.2021.)
Vancouver
Škarić V, Raza Z, Kašnar B. Synthesis and Intramolecular Rearrangement of Enantiomeric Amino-alcohols in the Aliphatic Thymidine Analogues Series. Croatica Chemica Acta [Internet]. 1986 [pristupljeno 24.06.2021.];59(1):297-306. Dostupno na: https://hrcak.srce.hr/177594
IEEE
V. Škarić, Z. Raza i B. Kašnar, "Synthesis and Intramolecular Rearrangement of Enantiomeric Amino-alcohols in the Aliphatic Thymidine Analogues Series", Croatica Chemica Acta, vol.59, br. 1, str. 297-306, 1986. [Online]. Dostupno na: https://hrcak.srce.hr/177594. [Citirano: 24.06.2021.]

Sažetak
The synthesis of (-)-1-(-3-amino-2-hydroxypropyl)thymine hydrochloride[(-)-(R)-(VIII)] by a catalytic hydrogenation of (-)-1-(3-
-azido-2-hydroxypropyl)thymine[(-)-(S)-(VII)] is described. The resolution of (2R)- and (2S)-(3j3-acetoxy-L\s-etienamidomethyl)-2,3'-
-dihydro-6-methyl-7H-oxazolo[3,2-a]pyrimidin-7-one[(2R)-(X) and
(2S)-(X)] by fractional crystallization, followed by the hydrolysis
of the resolved stereoisomers in 25% isopropanolic HCI afforded
the (+) and (-) amino-alcohol hydrochlorides VIlI, respectively,
The diastereoisomers X were prepared from (R,S)-2-aminomethyl-
2,3-dihydro-6-methyl-7H-oxazolo[3,2-a]pyrimidin-7-one (V)
and p-nitrophenyl 3j3-acetoxy-~5-etienate (XII) by the active ester
method. The conversion of X into VIlI proceeded via intramolecular
formation of (5R)- and (5S)-2-(313-acetoandrost-5-en-17-yl)-
-5-(thymin-1-yImethyl)oxazoline (XIII), accompanied by inversion
of configuration at the asymmetric C(2) centre. The purity of the
diastereoisomeric products X and XIII was determined by the
1H-NMR spectra.

Hrčak ID: 177594

URI
https://hrcak.srce.hr/177594

Posjeta: 184 *