Tetrahedron: Asymmetry

A concise synthesis of (2S, 3S)-BocAHPBA and (R)-BocDMTA, chiral building blocks for peptide-mimetic HIV protease inhibitors

M Ikunaka, J Matsumoto, Y Nishimoto

文献索引：Ikunaka, Masaya; Matsumoto, Jun; Nishimoto, Yukifumi Tetrahedron Asymmetry, 2002 ,  vol. 13,  # 11  p. 1201 - 1208

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被引用次数: 25

摘要

Scalable syntheses of (2S, 3S)-3-N-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (BocAHPBA) 1 and (R)-3-tert-butoxycarbonyl-5, 5-dimethyl-1, 3-thiazolidine-4- carboxylic acid (BocDMTA) 2 have been developed. Both 1 and 2 can serve as chiral building blocks in assembling JE-2147 (KNI-764) 3, a potent HIV protease inhibitor. The synthesis of (2S, 3S)-BocAHPBA 1 is achieved in 41% overall yield from (S)-2-N, N- ...