Use of optically active cyclic diethyl sulfamidate 2-phosphonates as chiral synthons for the synthesis of β-substituted α-amino phosphonates

Add time:08/08/2019    Source:sciencedirect.com

Optically active protected sulfamidate 2-phosphonates have been synthesized from either (R)- or (S)-N-benzyl-2-phosphonoserine for use as chiral synthons. These sulfamidates have been shown to undergo nucleophilic substitution with select nucleophiles, to afford following N-sulfate removal, the β-substituted α-amino-2-phosphonates. N-Sulfate removal was accomplished using boron trifluoride etherate in the presence of either n-propylthiol or N-hydroxysuccinimide allowing retention of the diethylphosphonate ester groups. Replacement of the unpleasant smelling n-propylthiol with N-hydroxysuccinimide provides higher yields of the desired products. Synthesis of β-S-substituted analogues required the use of cesium carbonate as a base. The sulfamidates described have excellent stability and have been demonstrated, using chiral HPLC, to be greater than 97% enantiomerically pure.

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