653589-54-9

Upstream product

• 653589-52-7 tert-butyl (2S,4S)-2-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(diphenyl)silyl]oxy}-6-hydroxyhexanoate 
• 653589-51-6 di(tert-butyl) (2S,4S)-4-{[tert-butyl(diphenyl)silyl]oxy}-6-oxo-1,2-piperidinedicarboxylate 
• 653589-16-3 di(tert-butyl) (2S,4S)-4-hydroxy-6-oxo-1,2-piperidinedicarboxylate 
• 653589-10-7 1,2-di-tert-butyl (2S)-4,6-dioxopiperidine-1,2-dicarboxylate 
• 34582-32-6 N-tert-butoxycarbonyl aspartic acid tert-butyl ester 

Downstream Products

• 1189372-41-5 C₃₁H₄₈N₂O₅Si 

Relevant academic research and scientific papers

Dual native chemical ligation at lysine

(Chemical Presented) A thiol group introduced on the γ-carbon of lysine mediates robust native chemical ligation at both the α- and ε-amines in two consecutive steps. Desulfurization then affords the final product, in which the lysine residue at the ligat

Synthesis of 4-mercapto-l-lysine derivatives: Potential building blocks for sequential native chemical ligation

A general and diastereoselective synthesis of (2S, 4S)-4-mercapto-l-lysine derivative was described. The key features of this synthesis include Zn-mediated diastereoselective Reformatsky reaction and selective reduction of methyl ester with sodium borohyd

Synthesis of Enantiopure 4-Hydroxypipecolate and 4-Hydroxylysine Derivatives from a Common 4,6-Dioxopiperidinecarboxylate Precursor

tert-Butyl 2-substituted 4,6-dioxo-1-piperidinecarboxylates 4 have been prepared in good yield starting from Boc-Asp-OtBu and other β-amino acids. By analogy with chiral tetramic acids, their reduction by NaBH4 in CH2Cl2/AcOH afforded the corresponding cis-4-hydroxy δ-lactams in good yield and stereoselectivity (68-98% de). In the absence of the A(1,3) strain (reduction of 6-substituted 2,4-dioxo-1-piperidines 7), the cis-4-hydroxy isomer was still obtained as the major product but the de values were consistently lower. 4-Hydroxy-6-oxo- 1,2-piperidinedicarboxylate 2a, readily accessible from Boc-Asp-OtBu (three steps, 63% overall yield), has proven to be an excellent building block for the synthesis of cis- and trans-4-hydroxypipecolates 17 and 24 (52 and 36% overall yield, respectively) and for the synthesis of a protected 4-hydroxylysine derivative 29 (41% overall yield).