132618-89-4Relevant academic research and scientific papers
Burgess Reagent Facilitated Alcohol Oxidations in DMSO
Sultane, Prakash R.,Bielawski, Christopher W.
, p. 1046 - 1052 (2018/06/18)
The Burgess reagent ([methoxycarbonylsulfamoyl]triethylammonium hydroxide) has historically found utility as a dehydrating agent. Herein we show that, in the presence of dimethyl sulfoxide, the Burgess reagent efficiently and rapidly facilitates the oxidation of a broad range of primary and secondary alcohols to their corresponding aldehydes and ketones in excellent yields and under mild conditions, and can be combined with other transformations (e.g., Wittig olefinations). A mechanism similar to those described for the Pfitzner-Moffatt and Swern oxidations is proposed.
Elative rates of Michael reactions of 2′-(phenethyl)thiol with vinyl sulfones, vinyl sulfonate esters, and vinyl sulfonamides relevant to vinyl sulfonyl cysteine protease inhibitors
Reddick, Jason J.,Cheng, Jianming,Roush, William R.
, p. 1967 - 1970 (2007/10/03)
(Matrix presented) The relative rates of Michael additions of 2′-(phenethyl)thiol to representative vinyl sulfonyl Michael acceptors were measured. The dependence of the reactivity of the Michael acceptor on the nature of the sulfonyl R substituent was determined in order to evaluate the effect of these substituents on the inactivation kinetics of comparably substituted vinyl sulfonyl cysteine protease inhibitors. The rates of these Michael additions vary over 3 orders of magnitude, with phenyl vinyl sulfonate esters (R = OPh) being ca. 3000-fold more reactive than N-benzyl vinyl sulfonamides (R = NHBn).
Design and synthesis of novel conformationally restricted HIV protease inhibitors
Salituro, Francesco G.,Baker, Christopher T.,Court, John J.,Deininger, David D.,Kim, Eunice E.,Li, Biquin,Novak, Perry M.,Rao, Bhisetti G.,Pazhanisamy,Porter, Margaret D.,Schairer, Wayne C.,Tung, Roger D.
, p. 3637 - 3642 (2007/10/03)
A set of HIV protease inhibitors represented by compound 2 has previously been described. Structural and conformational analysis of this compound suggested that conformational restriction of the P1/P2 portion of the molecule could lead to a novel set of potent protease inhibitors. Thus, probe compounds 3-7 were designed, synthesized, and found to be potent inhibitors of HIV protease.
A stereoselective synthesis of (3S,4S) statine and related compounds
Misiti,Zappia
, p. 7359 - 7362 (2007/10/02)
(3S,4S)Statine and (3S,4S)AHPPA were synthesized efficiently using a highly stereoselective iodocyclocarbamation of the chiral Z-olefins 6 and 6b derived from the correspondent α-aminoacids.
