Title
Synthesis of orthogonally protected (2S)-2-amino-adipic acid (α-AAA) and (2S,4R)-2-amino-4-hydroxyadipic acid (Ahad)
Document Type
Article
Publication Date
6-7-2013
Abstract
(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.
Publication Source (Journal or Book title)
The Journal of organic chemistry
First Page
5401
Last Page
9
Recommended Citation
Yadav, S., & Taylor, C. M. (2013). Synthesis of orthogonally protected (2S)-2-amino-adipic acid (α-AAA) and (2S,4R)-2-amino-4-hydroxyadipic acid (Ahad). The Journal of organic chemistry, 78 (11), 5401-9. https://doi.org/10.1021/jo400558t