183075-33-4Relevant academic research and scientific papers
Access to Anti or Syn 2-Amino-1,3-diol Scaffolds from a Common Decarboxylative Aldol Adduct
Chaumont, Pauline,Baudoux, Jérome,Maddaluno, Jacques,Rouden, Jacques,Harrison-Marchand, Anne
, p. 8081 - 8091 (2018)
A straightforward synthetic pathway allowing the access to anti or syn 2-amino-1,3-diol scaffolds is presented. The strategy relies on a diastereoselective organocatalyzed decarboxylative aldol reaction of a N-Boc-hemimalonate that is easily formed from commercial N-Boc-diethyl malonate. Although this method has been optimized previously with the N-Bz-hemimalonate analogue, this key step was reinvestigated with the N-Boc derivative to improve the required reaction time, the yield, and the diastereoselectivity. The new conditions enhance this transformation, and quantitative yields and anti/syn ratios up to 96:4 can be obtained. The anti aldol product was easily isolated in pure form and then taken forward as the key precursor in the preparation of both a set of ten N-/O-alkylated anti 2-amino-1,3-diol derivatives and the syn congeners.
Highly enantioselective synthesis of anti aryl β-hydroxy α-amino esters via DKR transfer hydrogenation
Liu, Zhuqing,Shultz, C.Scott,Sherwood, Candice A.,Krska, Shane,Dormer, Peter G.,Desmond, Richard,Lee, Claire,Sherer, Edward C.,Shpungin, Joseph,Cuff, James,Xu, Feng
scheme or table, p. 1685 - 1688 (2011/05/05)
An efficient preparation of highly enantiomerically enriched aryl β-hydroxy α-amino esters via dynamic kinetic resolution (DKR), asymmetric transfer hydrogenation of α-amino β-keto esters is described. The anti β-hydroxyl α-amino esters were obtained both in high yields and high diasteroselectivity. The observed high anti selectivity is inconsistent with the previous results in literature. The absolute stereochemistry of the aryl β-hydroxy α-amino esters was unambiguously confirmed via chemical derivatization as well as Vibrational Circular Dichroism (VCD) techniques.
Synthesis and evaluation of a difluoromethylene analogue of sphingomyelin as an inhibitor of sphingomyelinase
Yokomatsu, Tsutomu,Takechi, Hiroaki,Akiyama, Takeshi,Shibuya, Shiroishi,Kominato, Takaaki,Soeda, Shinji,Shimeno, Hiroshi
, p. 1277 - 1280 (2007/10/03)
A sphingomyelin analogue 2, in which the long alkenyl chain and the phosphodiester moiety of sphingomyelin were replaced by a phenyl and an isosteric difluoromethylenephosphonic acid, was prepared to evaluate its inhibitory potency to sphingomyelinase. The analogue non-competitively inhibited the neutral sphingomyelinase in bovine brain microsomes with an IC50 of 400 μM. The compound had the ability to suppress tumor necrosis factor α-induced apoptosis of PC-12 neurons at a low concentration of 0.1 μM.
Practical synthesis of threo-(1S, 2S)- and erythro-(1R, 2S)-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol (PPMP) from L-serine
Nishida, Atsushi,Sorimachi, Hiroshi,Iwaida, Mie,Matsumizu, Miyako,Kawate, Tomohiko,Nakagawa, Masako
, p. 389 - 390 (2007/10/03)
Both L-threo and D-erytho-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol (PPMP) were synthesized stereoselectively from L-serine.
Grignard reactions to chiral oxazolidine aldehydes
Williams, Lorenzo,Zhang, Zhongda,Shao, Feng,Carroll, Patrick J.,Joullie, Madeleine M.
, p. 11673 - 11694 (2007/10/03)
Modest to high levels of asymmetric induction are observed with Grignard additions to Garner type aldehydes. The resultant secondary alcohols are important precursors of chiral building blocks for asymmetric synthesis and we have demonstrated that they can be readily converted into their respective γ-hydroxy-β-amino alcohols and β-hydroxyamino acids. Additionally, aryloxy ethers, important components of many natural products, can be obtained from these precursors.
