Stereoselective Synthesis of 2-Amino-2-deoxy-D-arabinose and 2-Deoxy-D-ribose

Abstract

An efficient method for the Stereoselective synthesis of 2-amino-2-deoxy-D-arabinose and 2-deoxy-D-ribose is described.
The key step in this method was accomplished by the nucleophilic addition of methyl isocyanoacetate to 2, 3-O-isopropylidene-D-glyceraldehyde with high erytro-selectivity (nearly 100%).
Subsequent intermolecular cyclization predominantly gave the desired oxazoline derivative (trans-form), in which two new chiral centers were formed. The oxazoline derivative was efficiently converted to both 2-amino-2-deoxy-D-arabinose and 2-deoxy-D-ribose.