133039-06-2Relevant articles and documents
Synthesis of orthogonally protected (2S)-2-amino-adipic acid (α-AAA) and (2S,4 R)-2-amino-4-hydroxyadipic acid (Ahad)
Yadav, Saroj,Taylor, Carol M.
, p. 5401 - 5409 (2013/07/26)
(2S,4R)-2-Amino-4-hydroxyadipic acid (Ahad) building block 45 was synthesized in 11 steps and 6.5% overall yield from commercially available materials. Key steps in stereocontrol were an asymmetric conjugate addition employing a proline-based catalyst and a syn-selective intramolecular-conjugate addition of an oxygen nucleophile to an α,β-unsaturated ester. To enable incorporation of α-amino-adipic acid (α-AAA) and Ahad into peptides, a truly orthogonal protecting group scheme was developed, encompassing an allyloxycarbonyl (Alloc) carbamate for Nα, a tert-butyl ester for the δ-COOH, an acetol ester for the α-COOH, and a tert- butyldimethylsilyl ether for the γ-hydroxy group of Ahad.
A new, short and efficient synthesis of both enantiomers of carnitine
Bellamy,Bondoux,Dodey
, p. 7323 - 7326 (2007/10/02)
A short, efficient and enantioselective synthesis of both (R) and (S) enantiomers of carnitine is reported starting with (R) or (S) malic acid and involving a chemoselective reduction step.
