Practical and Efficient Synthesis of Orthogonally Protected α-2,3-Diaminopropionic Acid (2,3-Dap), 2,4-Diaminobutanoic Acid (2,4-Dab), and their N-Methylated Derivatives

The synthesis of orthogonally protected Fmoc-Dap/Dab (Boc/Z/Alloc)-OH starting from Fmoc-Asp/Glu has been described. The salient features of our synthetic strategy involved formation of Fmoc-Asp/Glu-5-oxazolidinone acids, conversion of acid function to acyl azides, Curtius rearrangement, and hydroly...

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Bibliographic Details
Published in:Synthetic communications 2006-09, Vol.36 (19), p.2901-2912
Main Authors: Rao, R. V. Ramana, Tantry, Subramanyam J., Babu, Vommina V. Suresh
Format: Article
Language:English
Subjects:
2,3-Dap and 2,4-Dab
Fmoc-strategy
microwave irradiation
N-Me derivatives
one-pot synthesis
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Summary:The synthesis of orthogonally protected Fmoc-Dap/Dab (Boc/Z/Alloc)-OH starting from Fmoc-Asp/Glu has been described. The salient features of our synthetic strategy involved formation of Fmoc-Asp/Glu-5-oxazolidinone acids, conversion of acid function to acyl azides, Curtius rearrangement, and hydrolysis of the oxazolidinone group.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910600772827