252919-53-2

Upstream product

• 100-39-0 benzyl bromide 
• 252919-51-0 4-benzyl 1-tert-butyl (3S)-2-allyl-3-(dibenzylamino)butanedioate 
• 252919-50-9 1-benzyl 4-tert-butyl (2S)-2-(dibenzylamino)butanedioate 
• 252919-52-1 1-benzyl 4-tert-butyl (2S,3S)-2-(dibenzylamino)-3-(3-hydroxypropyl)butanedioate 

Downstream Products

• 252919-54-3 (2S,3S)-3-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid 

Relevant academic research and scientific papers

TRIAZOLE-ISOXAZOLE COMPOUND AND MEDICAL USE THEREOF

A compound represented by Formula [I]: or pharmaceutically acceptable salt thereof, wherein each symbol is as defined in the description.

Asymmetric synthesis of trans-2,3-piperidinedicarboxylic acid and trans-3,4-piperidinedicarboxylic acid derivatives

Asymmetric syntheses of (2S,3S)-3-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (1b), (3R,4S)-4-(tert-butoxycarbonyl)-3-piperidinecarboxylic acid (2b), and their corresponding N-Boc and N-Cbz protected analogues 8a,b and 17a,b are described. Enantiomerically pure 1b has been synthesized in five steps starting from L-aspartic acid β-tert-butyl ester. Tribenzylation of the starting material followed by alkylation with allyl iodide using KHMDS produces the key intermediate 5a in a 6:1 diastereomeric excess. Upon hydroboration, the alcohol 6a is oxidized, and the resulting aldehyde 7 is subjected to a ring closure via reductive amination, providing 1b in an overall yield of 38%. Optically pure 2b has been synthesized beginning with N-Cbz-β-alanine. The synthesis involves the induction of the first stereogenic center using Evans's chemistry and sequential LDA-promoted alkylations with tert-butyl bromoacetate and allyl iodide. Further elaboration by ozonolysis and reductive amination affords 2b in an overall yield of 28%.