利用亚硝酸盐介导的Lattrell-Dax羟基翻转反应,合成了硫代基夫碱的叠氮基糖原料3,并探讨了不同邻位保护基对翻转反应的影响.结果表明:邻位羟基用三苯甲基(Tr)保护,化合物可以成功实现Lat-trell-Dax羟基翻转反应,得到单一构型产物.
[1] KAYAKIRI H, TAKESE S, SHIBATA T. Structure of kifunensine, a new immunomodulator isolated from an actinomycete [J]. Journal of Organic Chemistry 1989, 54.
[2] ELBEIN A D, TROPEA J E, MITCHELL M. Kifunensine, a potent inhibitor of the glycoprotein processing mannosidase I [J]. Journal of Biological Chemistry 1990, 265.
[3] Karaveg K, Moremen KW. Energetics of substrate binding and catalysis by class 1 (glycosylhydrolase family 47) alpha-mannosidases involved in N-glycan processing and endoplasmic reticulum quality control [J]. The Journal of biological chemistry 2005, 33(33).
[4] HERING K W, KARAVEG K, MOREMEN K W. A practical synthesis of kifunensine analogues as inhibitors of endoplasmic reticulum α-mannosidase I [J]. Journal of Organic Chemistry 2005, 70.
[5] Chen, H., Li, R., Liu, Z., Wei, S., Zhang, H., Li, X.. Synthesis of kifunensine thioanalogs and their inhibitory activities against HIV-RT and α-mannosidase [J]. Carbohydrate research 2013.
[6] Cosme G. Francisco, Raimundo Freire, Concepcion C. Gonzalez, Elisa I. Leon, Concepcion Riesco-Fagundo, Ernesto Suarez. Fragmentation of Carbohydrate Anomeric Alkoxy Radicals. Synthesisof Polyhydroxy Piperidines and Pyrrolidines Related to Carbohydrates [J]. The Journal of Organic Chemistry 2001, 5(5).
[7] Wang, GF, Zhang, W, Lu, ZC, Wang, P, Zhang, XL, Li, YX. Convenient Synthesis of an N-Glycan Octasaccharide of the Bisecting Type [J]. The Journal of Organic Chemistry 2009, 6(6).
[8] Suhara Y, Kittaka A, Ono K, Kurihara M, Fujishima T, Yoshida A, Takayama H. Design and efficient synthesis of new stable 1alpha, 25-dihydroxy-19-norvitamin D(3) analogues containing amide bond. [J]. Bioorganic and Medicinal Chemistry Letters 2002, 24(24).
[9] Hai Dong, Zhichao Pei, Olof Ramstrom. Stereospecific Ester Activation in Nitrite-Mediated Carbohydrate Epimerization [J]. The Journal of Organic Chemistry 2006, 8(8).
