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| Synthesis and Application of A New Photolabile Protecting Group for Phosphate Derivatives |
| LIU Shan-shan, MA Chi, LI Jun-ru, HONG Li-hong, ZHANG You-lai |
| College of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, China |
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Abstract 4-Oxo-3-phenyl-4H-thiochromene-2-carbaldehyde(4) was prepared by dehydration reaction, iodine substitution reaction, Suzuki-Miyaura coupling and oxidation， using thiophenol and ethyl acetoacetate as starting material. Furthermore oxidation of the sulfur atom of 4 with m-CPBA, and then reaction with TsNHNH2 to obtain tosylhydrazone(6). 2-Diazomethyl-3-phenyl-4H-thiochromen-4-one 1,1-dioxide(7) was synthesized by Bamford-Stevens reaction from 6. The structures were characterized by 1H NMR, 13C NMR and HR-MS. 7 was designed as a novel photolabile protecting group for the protection and photodeprotection of phosphate derivatives. Protection reaction proceeded smoothly under mild reaction. The photodeprotection yields were more than 95% in 15 min monitored by UV-Vis and fluorescence spectroscopies.
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Received: 23 November 2015
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2016, Vol. 24 
