Synfacts 2010(2): 0239-0239  
DOI: 10.1055/s-0029-1219056
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Solid-Phase Synthesis of Fmoc-α-Amino Phosphonic Acid Hexamer

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Toshihiro Watanabe
Y. Ishibashi, M. Kitamura*
Nagoya University, Japan
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Publikationsverlauf

Publikationsdatum:
21. Januar 2010 (online)

Significance

The authors reported a solid-phase synthesis of Fmoc-α-amino phosphonic acid benzyl ester hexamer 7. Thus, resin-supported allylic alcohol linker 3 was prepared by peptide condensation of 9-[(4-methoxyphenyl)diphenylmethoxy]-10-undecenoic acid (1) and TentaGel-NH2 2 with DIC and HOBt followed by deprotection. The resulting resin 3 was subjected to the dehydrative condensation with α-amino phosphonic acid 4 ­using DIPEA, HOAt and DIC to give the resin-­supported Fmoc-α-amino phosphonic acid 5. Five-time repetition of Fmoc-removal with piperidine and dehydrative condensation of 4 gave a resin-supported Fmoc-α-amino phosphonic acid hexamer 6. Detachment of an α-amino phosphonic acid hexamer with [RuCp(PPh3)(MeCN)2]PF6 gave the desired product 7.