4554-10-3

Upstream product

• 613-90-1 benzoyl cyanide 
• 27963-97-9 2-amino-(1,2-dideoxy-α-D-ribofurano)<1,2-d>-2-oxazoline 
• 81026-84-8 (3aS,5R,6R,6aR)-6-Hydroxy-5-hydroxymethyl-2-oxo-tetrahydro-furo[2,3-d]oxazole-3-carboxylic acid benzyl ester 
• 81026-82-6 2-Oxo-3-benzyloxycarbonyl-3',5'-di-O-benzoyl-α-D-ribofurano<1',2':4,5>-oxazolidin 

Relevant academic research and scientific papers

Protected Aminooxazolines of Arabinose and Ribose

The 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--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-acylderivatives 6.Mild hydrolysis of the benzyloxycarbonyl group with trifluoroacetic acid yields the 3',5'-di-O-acyl-D-arabino-(ribo)-furo--2-oxooxazolidines as further intermediates for the synthesis of nucleosides.