Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate

Beilstein Journal of Organic Chemistry

Shinichiro Fuse¹  Hisashi Masui²  Takashi Takahashi²  Sae Yosugi² 

[1] Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan;Yokohama University of Pharmacy, 601 Matano-cho, Totsuka-ku, Yokohama 245-0066, Japan,;

关键词: acetal formation;    amino acid;    automated synthesis;    Garner’s aldehyde;    reduction;   

DOI  :  10.3762/bjoc.13.13

来源: DOAJ

【 摘 要 】

A solution-phase automated synthesis of the versatile synthetic intermediate, Garner’s aldehyde, was demonstrated. tert-Butoxycarbonyl (Boc) protection, acetal formation, and reduction of the ester to the corresponding aldehyde were performed utilizing our originally developed automated synthesizer, ChemKonzert. The developed procedure was also useful for the synthesis of Garner’s aldehyde analogues possessing fluorenylmethyloxycarbonyl (Fmoc) or benzyloxycarbonyl (Cbz) protection.

【 授权许可】

Unknown