Synthesis of 2-substituted 3,4-bis(diethoxyphosphorylmethyl)furans

被引:6
作者
Pevzner, L. M. [1 ]
机构
[1] Tech Univ, St Petersburg State Technol Inst, St Petersburg 190031, Russia
关键词
diphosphonate; synthesis; 2,4,5-substituted furan; furancarboxylic acid derivative; BISPHOSPHONATES; ACID;
D O I
10.1134/S1070363215020139
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Bromination of ethyl 4-(diethoxyphosphorylmethyl)-5-methylfuran-2-carboxylate and 4-(diethoxyphosphorylmethyl)-5-methylfuran-2-carbonitrile with N-bromosuccinimide followed by phosphorylation via the Arbuzov reaction have yielded the corresponding 2-substituted 4,5-bis(diethoxyphosphorylmethyl)furans. Synthesis and transformations of bisphosphorylated 2-furoic acid and its derivatives are described.
引用
收藏
页码:428 / 435
页数:8
相关论文
共 8 条
[1]   Structural aspects of the effectiveness of bisphosphonates as competitive inhibitors of the plant vacuolar proton-pumping pyrophosphatase [J].
Gordon-Weeks, R ;
Parmar, S ;
Davies, TGE ;
Leigh, RA .
BIOCHEMICAL JOURNAL, 1999, 337 :373-377
[2]   Bisphosphonates target multiple sites in both cis- and trans-prenyltransferases [J].
Guo, Rey-Ting ;
Cao, Rong ;
Liang, Po-Huang ;
Ko, Tzu-Ping ;
Chang, Tao-Hsin ;
Hudock, Michael P. ;
Jeng, Wen-Yih ;
Chen, Cammy K. -M. ;
Zhang, Yonghui ;
Song, Yongcheng ;
Kuo, Chih-Jung ;
Yin, Fenglin ;
Oldfield, Eric ;
Wang, Andrew H. -J. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (24) :10022-10027
[3]   Chloroalkylation of (diethoxyphosphinoylmethyl)furans [J].
Pevzner, L. M. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2008, 78 (02) :206-209
[4]   Enol phosphates of phosphorylated derivatives of furylacetic aldehyde and furylpiruvic acid [J].
Pevzner, L. M. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2014, 84 (11) :2147-2159
[5]   Synthesis of phosphonomethylated acid chlorides, alcohols, and aldehydes of the furan series [J].
Pevzner, L. M. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2011, 81 (08) :1620-1628
[6]   Diethoxyphosphorylmethylfurans in Curtius reaction [J].
Pevzner, L. M. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2011, 81 (01) :56-70
[7]  
PEVZNER LM, 2000, ZH OBSHCH KHIM, V70, P27
[8]   Structure-based design of an osteoclast-selective, nonpeptide Src homology 2 inhibitor with in vivo antiresorptive activity [J].
Shakespeare, W ;
Yang, M ;
Bohacek, R ;
Cerasoli, F ;
Stebbins, K ;
Sundaramoorthi, R ;
Azimioara, M ;
Vu, C ;
Pradeepan, S ;
Metcalf, C ;
Haraldson, C ;
Merry, T ;
Dalgarno, D ;
Narula, S ;
Hatada, M ;
Lu, XD ;
van Schravendijk, MR ;
Adams, S ;
Violette, S ;
Smith, J ;
Guan, W ;
Bartlett, C ;
Herson, J ;
Iuliucci, J ;
Weigele, M ;
Sawyer, T .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2000, 97 (17) :9373-9378