104418-82-8Relevant academic research and scientific papers
Synthesis, Biological Activity, and Conformational Analysis of (2S,3R,4S)-MeBmt1-cyclosporin, a Novel 1-Position Epimer of Cyclosporin A
Rich, Daniel H.,Sun, Chong-Qing,Guillaume, Dominique,Dunlap, Brian,Evans, David A.,Weber, Ann E.
, p. 1982 - 1987 (1989)
Cyclosporin A (CsA, 1), an immunosuppressive cyclic undecapeptide, contains a unique amino acid, (4R)-4--4,N-dimethyl-L-threonine (MeBmt), that appears to be critically involved in the biological activity of CsA.In order to further explore th
Asymmetric Glycine Enolate Aldol Reactions: Synthesis of Cyclosporine's Unusual Amino Acid, MeBmt
Evans, David A.,Weber, Ann E.
, p. 6757 - 6761 (2007/10/02)
The chiral glycine synthon, 3c, as its derived stannous enolate, has been demonstrated to undergo a highly syn diastereoselective aldol addition reaction with representative aldehydes to give the adducts 5 (R = C6H5, Me, Me2CH) in yields ranging from 71 to 92percent.The utility of these intermediates has been demonstrated via the subsequent three-step transformation of these adducts to the enantiomerically pure N-methyl β-hydroxy amino acids 1.This reaction methodology has been applied to the asymmetric synthesis of (4R)-4-((E)-2-butenyl)-4,N-dimethyl-L-threonine (1a), an important constituent in the immunosuppressant peptide cyclosporine.Several additional structural analogues of 1a were also prepared in conjunction with this study.
