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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

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.

Ključne riječi

Hrčak ID:

177594

URI

https://hrcak.srce.hr/177594

Datum izdavanja:

16.5.1986.

Posjeta: 867 *