Synthesis of Non-Symmetric Functionalized Polyfluoroalkyl
Phosphites
摘要:
Two ways for the synthesis of new representatives of non-symmetric organic phosphites with polyfluoroalkyl substituents were developed based on organic dichlorophosphites. The reaction of polyfluoroalkyl dichlorophosphites with allyl alcohol, proceeding at a temperature of -10-22 degrees C (2 h) in the presence of triethylamine, gave diallyl polyfluoroalkyl phosphites in a yield of 75-77%. Under similar conditions (-30-22 degrees C, 2-4 h, Et3N), alkyl (or aryl) dichlorophosphites reacted with polyfluoroalkanols to form alkyl (or aryl) bis(polyfluoroalkyl) phosphites (yield 56-67%). Unlike diallylpolyfluoroalkyl- and alkylbis(polyfluoroalkyl) phosphites, arylbis(polyfluoroalkyl) phosphites are symmetrized under storage conditions (room temperature, inert atmosphere), forming the corresponding triaryl- and tris(polyfluoroalkyl) phosphites.
[reaction: see text] Highly efficient rhodium-catalyzed asymmetric addition of arylboronicacids to aldehydes has been realized by using chiral spiro monophosphite ligands, affording diarylmethanols in excellent yields and good enantiomeric excesses.
Arbuzov reaction of arylphosphorodichloridite with mixture of one equivalent of AZT or d4T and one equivalent of tert-butyl alcohol led to the corresponding AZT/d4T aryl H-phosphonate diesters, and the following reactionof the H-phosphonate diesters with amino acid methyl esters in the presence of N-chloro-succinimide (NCS) produced membrane-soluble anti-HIV prodrugs AZT/d4T aryl phosphoramidate derivatives
芳基二氯化磷与一当量 AZT 或 d4T 和一当量叔丁醇的混合物的 Arbuzov 反应产生相应的 AZT/d4T 芳基 H-膦酸二酯,H-膦酸二酯与氨基酸甲酯的以下反应N-氯-琥珀酰亚胺 (NCS) 的存在以良好的产率产生了膜溶性抗 HIV 前药 AZT/d4T 芳基氨基磷酸酯衍生物。
Kazantseva, M. V.; Timokhin, B. V.; Donskikh, V. I., Journal of general chemistry of the USSR, 1991, vol. 61, # 4.2., p. 932
作者:Kazantseva, M. V.、Timokhin, B. V.、Donskikh, V. I.
DOI:——
日期:——
KAZANTSEVA, M. V.;TIMOXIN, B. V.;DONSKIX, V. I., ZH. OBSHCH. XIMII, 61,(1991) N, S. 53-54
作者:KAZANTSEVA, M. V.、TIMOXIN, B. V.、DONSKIX, V. I.