57280-22-5Relevant articles and documents
Divergent approach to the synthesis of (-)-balanol heterocycle and cis-3-hydroxypipecolic acid based on chiral 2-aminoalkanol equivalent
Chavan, Subhash P.,Kalbhor, Dinesh B.,Gonnade, Rajesh G.
, (2021/01/14)
Enantioselective synthesis of the hexahydroazepine core of (?)-balanol and formal synthesis of cis-3-hydroxypipecolic acid from a common intermediate have been accomplished by a divergent path. The common intermediate was accessed from a favorably protected enantiomerically pure 2-amino-1,3,4-butanetriol (ABT) equivalent via oxidation and Wittig olefination. The synthesis of (?)-balanol heterocycle featured tandem reduction/acetal-deprotection/γ-lactonization reaction and a one-pot azide reduction followed by seven membered aza-heterocycle formation while the route to cis-3-hydroxypipecolic acid highlighted the base induced piperidine ring formation and regioselective benzylidine-acetal cleavage.
The synthesis of the 2, 3-difluorobutan-1, 4-diol diastereomers
Szpera, Robert,Kovalenko, Nadia,Natarajan, Kalaiselvi,Paillard, Nina,Linclau, Bruno
, p. 2883 - 2887 (2018/01/17)
The diastereoselective synthesis of fluorinated building blocks that contain chiral fluorine substituents is of interest. Here we describe optimisation efforts in the synthesis of anti-2, 3-difluorobutane-1, 4-diol, as well as the synthesis of the corresponding syn-diastereomer. Both targets were synthesised using an epoxide opening strategy.
Production method of optically active amino alcohols
-
, (2008/06/13)
A method for producing an optically active amino alcohol compound of the formula [3], an enantiomer thereof or a salt thereof, comprising reacting a mesoepoxide compound of the formula [1] with a compound of the formula [2] in the presence of a mixed catalyst comprising a Lewis acid and a proton donor: wherein R1, R2and R3are each H, an optionally substituted lower alky, and the like, or R1and R1or R2and R3may form an optionally substituted ring; and R4and R5are each H, an optionally substituted lower alkyl, and the like, or R4and R5may form an optionally substituted ring together with the adjacent N, or an imide group or azide group together with the adjacent N, and R6is H or a silyl group. The present invention enables stereoselective production of a desired intermediate compound, which is an HIV protease inhibitor, extremely efficiently as compared to conventional methods. The method of the present invention is a very useful method which can be used not only for the production of said intermediate compound but also for the production of various other compounds.