Stereoselective Syntheses of (E)-. ALPHA.,. BETA.-Didehydroamino Acid and Peptide Containing Its Residue Utilizing Oxazolidinone Derivative

M Kometani, K Ihara, R Kimura…

Index: Kometani, Miki; Ihara, Kohki; Kimura, Rumi; Kinoshita, Hideki Bulletin of the Chemical Society of Japan, 2009 , vol. 82, # 3 p. 364 - 380

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Citation Number: 7

Abstract

Reaction of methyl N-Boc-N-phenoxycarbonylglycinate with various aldehydes afforded the corresponding cis-4, 5-oxazolidinone derivatives, which were effectively converted to (E)-α, β-didehydroamino acids by means of a base. Furthermore, N-deprotection of the oxazolidinone derivatives and subsequent coupling reaction with Boc-amino acid furnished the corresponding dipeptides, which were transformed to dipeptide containing α, β- ...

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