(3S,4R,5R)-3-(2-Hydroxyethyl)piperidine-3,4,5-triol as an isofagomine analogue: synthesis and glycosidase inhibition study
作者： Preeti Gupta , Suresh Dharuman , Yashwant D. Vankar
DOI: 10.1016/J.TETASY.2010.11.027
关键词:
摘要: The synthesis of (3S,4R,5R)-3-(2-hydroxyethyl)piperidine-3,4,5-triol 10 has been described from D-glucose. base promoted cyclization for the construction piperdine framework is key step synthesis.
elsevier.com
sci-hub.se 参考文章(37)
G.B. Karlsson, T.D. Butters, R.A. Dwek, F.M. Platt, Effects of the imino sugar N-butyldeoxynojirimycin on the N-glycosylation of recombinant gp120. Journal of Biological Chemistry. ,vol. 268, pp. 570- 576 ,(1993) , 10.1016/S0021-9258(18)54189-2
Jian-Qiang Fan, Satoshi Ishii, Naoki Asano, Yoshiyuki Suzuki, Accelerated transport and maturation of lysosomal alpha-galactosidase A in Fabry lymphoblasts by an enzyme inhibitor. Nature Medicine. ,vol. 5, pp. 112- 115 ,(1999) , 10.1038/4801
Yoshitaka Ichikawa, Yasuhiro Igarashi, Mie Ichikawa, Yoshitomo Suhara, 1-N-Iminosugars: Potent and Selective Inhibitors of β-Glycosidases Journal of the American Chemical Society. ,vol. 120, pp. 3007- 3018 ,(1998) , 10.1021/JA973443K
Vasant V Ranade, Iminosugars-From Synthesis to Therapeutic Applications American Journal of Therapeutics. ,vol. 16, pp. 200- ,(2009) , 10.1097/MJT.0B013E318172886D
Nitin T Patil, Sheeja John, Sushma G Sabharwal, Dilip D Dhavale, None, 1-Aza-sugars from D-glucose. Preparation of 1-deoxy-5-dehydroxymethyl-nojirimycin, its analogues and evaluation of glycosidase inhibitory activity. Bioorganic & Medicinal Chemistry. ,vol. 10, pp. 2155- 2160 ,(2002) , 10.1016/S0968-0896(02)00073-1
Anne Bülow, Igor W. Plesner, Mikael Bols, A Large Difference in the Thermodynamics of Binding of Isofagomine and 1-Deoxynojirimycin to β-Glucosidase Journal of the American Chemical Society. ,vol. 122, pp. 8567- 8568 ,(2000) , 10.1021/JA001762X
E. J. COREY, K. C. NICOLAOU, Richard D. BALANSON, Yoshimasa MACHIDA, A Useful Method for the Conversion of Azides to Amines Synthesis. ,vol. 1975, pp. 590- 591 ,(1975) , 10.1055/S-1975-23843
Venkata Ramana Doddi, Yashwant D. Vankar, Synthesis of Pyrrolidine‐Based Imino Sugars as Glycosidase Inhibitors European Journal of Organic Chemistry. ,vol. 2007, pp. 5583- 5589 ,(2007) , 10.1002/EJOC.200700719
Takashi L. Suyama, William H. Gerwick, Practical Total Syntheses of Epiquinamide Enantiomers Organic Letters. ,vol. 8, pp. 4541- 4543 ,(2006) , 10.1021/OL061736P
N. Asano, Sugar-mimicking glycosidase inhibitors: bioactivity and application Cellular and Molecular Life Sciences. ,vol. 66, pp. 1479- 1492 ,(2009) , 10.1007/S00018-008-8522-3