169767-83-3Relevant academic research and scientific papers
α- and β-Homogalactonojirimycins (α- and β-Homogalactostatins): Synthesis and further biological evaluation
Martin, Olivier R.,Saavedra, Oscar M.,Xie, Fang,Liu, Li,Picasso, Sylviane,Vogel, Pierre,Kizu, Haruhisa,Asano, Naoki
, p. 1269 - 1278 (2007/10/03)
The homoiminosugars α- and β-homogalactonojirimycins were prepared from a common intermediate, tetra-O-benzyl-D-galacto-heptenitol 6, by way of highly stereoselective reaction sequences involving, as the key steps, an internal amidomercuration (α-epimer) and a double reductive amination (β-epimer). α-Homogalactonojirimycin retains a large part of the potent activity of the parent galactonojirimycin and 1-deoxygalactonojirimycin as an inhibitor of α-galactosidases. However, by contrast with the parent iminosugars, it does not inhibit β-galactosidases, with the exception of the Jack beans enzyme. β-Homogalactonojirimycin is a weak α-galactosidase inhibitor and is completely devoid of activity towards β-galactosidases. Thus, a marked selectivity toward one family of enzymes has been achieved by the addition of an α-CH2OH group in the structure of the parent iminosugars.
Synthesis of 'α-homogalactostatin' and of its 1,N-anhydro derivative
Martin,Liu,Xie
, p. 4027 - 4030 (2007/10/02)
α-Homogalactostatin 2 was prepared in 10 steps from 2,3,4,6-tetra-O-benzyl-D-galactose by way of a Wittig chain extension and a mercuricyclization. The synthesis of 2 was assisted by the unexpected participation of the nitrogen protecting group (benzyl ca
