1374977-59-9Relevant academic research and scientific papers
Stereochemistry of 1,5-benzothiazepin-4-one S-oxide: Insight into the stereogenic elements at the sulfur atom and axis
Tabata, Hidetsugu,Yoneda, Tetsuya,Oshitari, Tetsuta,Takahashi, Hideyo,Natsugari, Hideaki
, p. 6264 - 6270 (2013/07/26)
Oxidation of 1,5-benzothiazepin-4-one (5-A) stereoselectively afforded the S-oxide 8I-A (aS,1S) in preference to the diastereomer 8II-A (aS,1R) affected by the remote stereogenic axis. All the enantiomers (8I-A/8I-B and 8II-A/8II-B) were separated and isolated, and the interconversion between 8I and 8II (equilibrium ratio ≈5:1) was unequivocally verified to be caused by the rotation around the axis.
Active conformation of seven-membered-ring benzolactams as new ACAT inhibitors: Latent chirality at N5 in the 1,5-benzodiazepin-2-one nucleus
Tabata, Hidetsugu,Wada, Naoya,Takada, Yuko,Nakagomi, Jun,Miike, Tomohiro,Shirahase, Hiroaki,Oshitari, Tetsuta,Takahashi, Hideyo,Natsugari, Hideaki
supporting information; experimental part, p. 1572 - 1576 (2012/04/10)
Nitrogen chirality: Potent new ACAT inhibitors with seven-membered-ring benzolactams as the core structures were first prepared, and the axial chirality recognized by the enzyme was clarified (e.g., 1; see scheme). The chirality at the axis (aS) of 1 controls the conformation of the entire lactam ring, causing the N5-CH3 to arrange in a pseudo-equatorial position (i.e., the amine at N5 is a chiral center with the S-configuration) both in the crystal state and in solution. Copyright
