24716-92-5Relevant academic research and scientific papers
Solid-phase synthesis of 6,7-cycloalkane-fused 1,4-diazepane-2,5-diones via a cyclization/release strategy
Caroen, Jurgen,Clemmen, An,Kámán, Judit,Backaert, Fréderique,Goeman, Jan L.,Fül?p, Ferenc,Van Der Eycken, Johan
, p. 148 - 160 (2015/12/23)
A solid-phase synthesis procedure for the parallel preparation of 6,7-cycloalkane-fused 1,4-diazepane-2,5-diones is described. The methodology applies α- and alicyclic β-amino acid building blocks to construct the seven-membered heterocyclic core, while a
The first direct enzymatic hydrolysis of alicyclic β-amino esters: A route to enantiopure cis and trans β-amino acids
Forro, Eniko,Fueloep, Ferenc
, p. 6397 - 6401 (2008/02/13)
The first direct enzymatic method is reported for the synthesis of cis and trans βamino acid enantiomers through the lipase-catalyzed enantioselective hydrolysis of alicyclic β esters in organic media. High enantioselectivities (E usually > 001) were observed when the Candida antarctica lipase B catalyzed reactions were performed with H2O (0.5 equivalents) in iP iPr2O at 5°C. The resolved products, obtained in good yields (≥42%), could be easily separated.
Large-scale syntheses of FMOC-protected non-proteogenic amino acids: Useful building blocks for combinatorial libraries
Dener, Jeffrey M.,Fantauzzi, Pascal P.,Kshirsagar, Tushar A.,Kelly, Daphne E.,Wolfe, Aaron B.
, p. 445 - 449 (2013/09/07)
Convenient and reliable large-scale procedures for the protection of various amino acids with N-(9-fluorenylmethoxycarbonyl)oxysuccinimide (FMOC-OSu) are described. Commercially available 4-aminomethylbenzoic acid and trans-4-(aminomethyl)cyclohexanecarbo
Structure-based design and synthesis of phosphinate isosteres of phosphotyrosine for incorporation in Grb2-SH2 domain inhibitors. Part 1
Furet, Pascal,Caravatti, Giorgio,Denholm, Alastair A.,Faessler, Alex,Fretz, Heinz,Garcia-Echeverria, Carlos,Gay, Brigitte,Irving, Ed,Press, Neil J.,Rahuel, Joseph,Schoepfer, Joseph,Walker, Clive V.
, p. 2337 - 2341 (2007/10/03)
Based on X-ray crystal structure information, mono charged phosphinate isosteres of phosphotyrosine have been designed and incorporated in a short inhibitory peptide sequence of the Grb2-SH2 domain. The resulting compounds, by exploiting additional interactions, inhibit binding to the Grb2-SH2 domain as potently as the corresponding doubly charged (phosphonomethyl)phenylalanine analogue. (C) 2000 Elsevier Science Ltd.
EXPERIMENTAL STUDIES OF THE ANOMERIC EFFECT. PART 2 RING INVERSION AND NITROGEN INVERSION EQUILIBRIA IN CIS-DECAHYDROQUINAZOLINES
Booth, Harold,Khedhair, Khedhair A.,Al-Shirayda, Hatif A. R. Y.
, p. 1465 - 1476 (2007/10/02)
The positions of conformational equilibria due to the double ring inversion in cis-decahydroquinazoline (7-->//07-->8 1.08 kcal mol-1; -ΔG09-->10 1.10 kcal mol-1) for the conformation which would allow the lone pairs on N(1) and N(3) to lie on the hindered 'inside' face of the molecules.However, the values of 3J(CHNH) coupling constants for both cis-decahydro-3-methylquinazoline (10) and cis (4aH, 8aH) cis (2H, 8aH)-decahydro-2,3-dimethylquinazoline (14) show that the N-inversion equilibrium at N(1) prefers the conformation in which N(1)-H is 'inside' (axial), and N(1)-lone pair equatorial, thus demonstrating the ability of the anomeric effect to outweigh steric repulsions.
Preparations and Crystal Structures of the 2-Oxides of Some Octahydro-3,2,1-benzoxathiazines and Octahydro-2H-3,1,2-benzoxazaphosphorines
Goodridge, Richard J.,Hambley, Trevor W.,Ridley, Damon D.
, p. 591 - 604 (2007/10/02)
The cis- and trans-fused 1-benzyl-1,4,4a,5,6,7,8,8a-octahydro-3,2,1-benzoxathiazine 2-oxides and cis- and trans-fused 1-benzyl-2-phenyl-1,4,4a,5,6,7,8,8a-octahydro-2H-3,1,2-benzoxazaphosphorine 2-oxides have been prepared from the cis- and trans-2-benzylaminocyclohexanemethanols and their structures have been determined by n.m.r. and crystallographic methods.
