653589-52-7Relevant academic research and scientific papers
Synthesis of 4-mercapto-l-lysine derivatives: Potential building blocks for sequential native chemical ligation
Pasunooti, Kalyan Kumar,Yang, Renliang,Vedachalam, Seenuvasan,Gorityala, Bala Kishan,Liu, Chuan-Fa,Liu, Xue-Wei
supporting information; experimental part, p. 6268 - 6271 (2010/04/28)
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
Marin,Didierjean,Aubry,Casimir,Briand,Guichard
, p. 130 - 141 (2007/10/03)
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).
