ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Protected Aminooxazolines of Arabinose and RiboseThe reaction of D-arabinose or D-ribose with cyanamide afforded 2-amino-1,2-oxazolines 1 which were treated with dihydropyran or ethylvinylether. In the presence of PTS the 3′,5′-di-THP- or 3′,5′-di-O-ethoxyethyl-D-arabino-(ribo)-furo-[1′,2′:4,5]-2-oxazolines 2 and 3 could be isolated as useful intermediates for the preparation of nucleosides.When the 2-aminooxazolines are treated with benzyloxycarbonylchloride or its p-substituted derivatives the N-3 atom of the oxazoline ring is preferentially substituted. Under these conditions the exocyclic amino function is always replaced and 2-oxo-3-benzyloxycarbonylderivatives 4 are obtained; only traces of the corresponding 2-aminoderivatives 5 are formed. Treatment of 4 with acetic anhydride, benzoylchloride, and benzoylcyanide, respectively, results in the 3′-, 5′-di-O-acyl derivatives 6. Mild hydrolysis of the benzyloxycarbonyl group with trifluoroacetic acid yields the 3′,5′-di-O-acyl-D-arabino-(ribo)-furo-[1′,2′:4,5]-2-oxooxazolidines as further intermediates for the synthesis of nucleosides.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19813230507
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