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Use of Optically Active Cyclic Diethyl Sulfamidate 2-Phosphonates as Chiral Synthons for the Synthesis of β-Substituted α-Amino Phosphonates by E. Kurt Dolence; Gabriele Mayer; Brenda D. Kelly is a Chemistry article available to read on EtoBox.

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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 b-substituted a-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 b-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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Author

E. Kurt Dolence; Gabriele Mayer; Brenda D. Kelly

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0957-4166)

Published

2005

Language

EN

Field

Chemistry (Physical Sciences)