132377-72-1Relevant academic research and scientific papers
Practical, scalable, enantioselective synthesis of (2R,3R)-N-boc-2-amino-3- cyclohexyl-3-hydroxypropanoic acid
Alonso, Monica,Santacana, Ferran,Rafecas, Llorenc,Riera, Antoni
, p. 690 - 693 (2012/12/25)
An enantioselective synthesis of (2R,3R)-2-(tert-butoxycarbonyl)amino-3- cyclohexyl-3-hydroxypropanoic acid has been described starting from enantiomerically enriched ethyl 3-cyclohexyl-2,3-dihydroxypropanoate, easily available by Sharpless asymmetric dih
Selective Transformations of threo-2,3-Dihydroxy Esters
Fleming, Paul R.,Sharpless, K. Barry
, p. 2869 - 2875 (2007/10/02)
Two highly regio- and stereoselective transformations of threo-2,3-dihydroxy esters have been developed.In the first reaction, the α-hydroxy group is converted into a sulfonate group (tosylate or nosylate); the α-tosylates and α-nosylates are then subjected to basic conditions (K2CO3/ROH) to give erythro glycidic esters in high yield.The α-nosylates are also suitable electrophiles for azides, giving access to erythro-α-azido-β-hydroxy esters.The second reaction involves conversion of the diol esters to acetoxy bromo esters.The β-subsituent plays a key role in determining the regiochemistry since cases with β-alkyl substituents afford β-acetoxy-α-bromo esters exclusively, whereas a β-phenyl substitutent directs formation of the α-acetoxy-β-bromo ester.The acetoxy bromo esters can subsequently be converted to the threo glycidic esters (via the bromohydrin esters); selective hydrogenolysis of the bromine substituent can also be achieved.
