An efficient synthesis of δ-glyconolactams by intramolecular Schmidt–Boyer reaction under microwave radiation

作者: Hua Chen , Rui Li , Fang Gao , Xiaoliu Li

DOI: 10.1016/J.TETLET.2012.10.098

关键词:

摘要: Abstract δ-Glyconolactams were first synthesized by the intramolecular Schmidt–Boyer reaction using corresponding δ-azidosugars as starting material. The could be efficiently performed in good yields of 61–69% under microwave radiation acid condition, providing an alternative protocol to iminosugar δ-lactam.

参考文章(26)
Cosme G. Francisco, Raimundo Freire, Concepción C. González, Elisa I. León, Concepción Riesco-Fagundo, Ernesto Suárez, Fragmentation of carbohydrate anomeric alkoxy radicals. synthesis of polyhydroxy piperidines and pyrrolidines related to carbohydrates. Journal of Organic Chemistry. ,vol. 66, pp. 1861- 1866 ,(2001) , 10.1021/JO0057452
Stefan Bräse, Carmen Gil, Kerstin Knepper, Viktor Zimmermann, Organic Azides: An Exploding Diversity of a Unique Class of Compounds Angewandte Chemie. ,vol. 44, pp. 5188- 5240 ,(2005) , 10.1002/ANIE.200400657
Michal Szostak, Lei Yao, Jeffrey Aubé, Cation-n control of regiochemistry of intramolecular Schmidt reactions en route to bridged bicyclic lactams. Organic Letters. ,vol. 11, pp. 4386- 4389 ,(2009) , 10.1021/OL901771B
Mattie S.M. Timmer, Martijn D.P. Risseeuw, Martijn Verdoes, Dmitri V. Filippov, Jasper R. Plaisier, Gijsbert A. van der Marel, Herman S. Overkleeft, Jacques H. van Boom, Synthesis of functionalized heterocycles via a tandem Staudinger/aza-Wittig/Ugi multicomponent reaction Tetrahedron: Asymmetry. ,vol. 16, pp. 177- 185 ,(2005) , 10.1016/J.TETASY.2004.11.079
George W.J. Fleet, Neil M. Carpenter, Sigthor Petursson, Nigel G. Ramsdena, Synthesis of deoxynojirimycin and of nojirimycin δ-lactam Tetrahedron Letters. ,vol. 31, pp. 409- 412 ,(1990) , 10.1016/S0040-4039(00)94568-4
Yoshio Nishimura, Hayamitsu Adachi, Takahiko Satoh, Eiki Shitara, Hikaru Nakamura, Fukiko Kojima, Tomio Takeuchi, All Eight Stereoisomeric d-Glyconic-δ-lactams: Synthesis, Conformational Analysis, and Evaluation as Glycosidase Inhibitors Journal of Organic Chemistry. ,vol. 65, pp. 4871- 4882 ,(2000) , 10.1021/JO000141J
M. Isabel García-Moreno, Carmen Ortiz Mellet, José M. García Fernández, Synthesis of Calystegine B2, B3, and B4 Analogues: Mapping the Structure‐Glycosidase Inhibitory Activity Relationships in the 1‐Deoxy‐6‐oxacalystegine Series European Journal of Organic Chemistry. ,vol. 2004, pp. 1803- 1819 ,(2004) , 10.1002/EJOC.200300731
Xiaoliu Li, Zhengang Zhu, Kefang Duan, Hua Chen, Zhiwei Li, Zhe Li, Pingzhu Zhang, Efficient and structurally controlled synthesis of novel polyhydroxylated indolizidine derivatives with an amino group Tetrahedron. ,vol. 65, pp. 2322- 2328 ,(2009) , 10.1016/J.TET.2009.01.026
Manohar Puppala, Annamalai Murali, Sundarababu Baskaran, Concise enantioselective construction of a bridged azatricyclic framework via domino semipinacol–Schmidt reaction Chemical Communications. ,vol. 48, pp. 5778- 5780 ,(2012) , 10.1039/C2CC31906C