Transetherification on polyols by intra- and intermolecular nucleophilic substitutions.

作者: Takahiro Muraoka , Kota Adachi , Rainy Chowdhury , Kazushi Kinbara

DOI: 10.1371/JOURNAL.PONE.0091912

关键词: TosylPolyolChemistryMedicinal chemistryLeaving groupTriolHydroxymethylYield (chemistry)NucleophilePentaerythritol

摘要: Transetherification on polyols involving intra- and intermolecular nucleophilic substitutions is reported. Di- or trialkoxide formation of propane-1,3-diol 2-(hydroxymethyl)propane-1,3-diol derivatives by NaH triggers the reaction via oxetanes formation, where order to add a polyol significantly influences yields products. It was demonstrated that protective group pentaerythritol skeleton apparently transferred hydrophilic hydrophobic chain molecules bearing leaving in one-step, conversion from tosyl benzyl successful using benzyl-appending triol afford desired product 67% yield.

参考文章(45)
Manash P. Sarmah, Mysore S. Shashidhar, Sulfonate protecting groups.: Improved synthesis of scyllo-inositol and its orthoformate from myo-inositol Carbohydrate Research. ,vol. 338, pp. 999- 1001 ,(2003) , 10.1016/S0008-6215(03)00052-1
Peter G. M. Wuts, Theodora W. Greene, Greene's Protective Groups in Organic Synthesis ,(2006)
Peter G. M. Wuts, Theodora W. Greene, Protective groups in organic synthesis ,(1981)
Bas GG Lohmeijer, Geraud Dubois, Frank Leibfarth, Russell C Pratt, Fredrik Nederberg, Alshakim Nelson, Robert M Waymouth, Charles Wade, James L Hedrick, Organocatalytic Living Ring-Opening Polymerization of Cyclic Carbosiloxanes Organic Letters. ,vol. 8, pp. 4683- 4686 ,(2006) , 10.1021/OL0614166
Yu Song, Yajun Duan, Lianyong Wang, Gustav Steinhoff, Deling Kong, Yaoting Yu, Yanming Wang, Weiling Kong, Polyamidoamine dendrimers with a modified Pentaerythritol core having high efficiency and low cytotoxicity as gene carriers. Biomacromolecules. ,vol. 10, pp. 617- 622 ,(2009) , 10.1021/BM801333S
Lin Li, Xiaoqin Shen, Qing-Hua Xu, Shao Q. Yao, A Switchable Two‐Photon Membrane Tracer Capable of Imaging Membrane‐Associated Protein Tyrosine Phosphatase Activities Angewandte Chemie. ,vol. 52, pp. 424- 428 ,(2013) , 10.1002/ANIE.201205940
Abel Garcia-Bernabé, Michael Krämer, Bèla Olàh, Rainer Haag, Syntheses and phase-transfer properties of dendritic nanocarriers that contain perfluorinated shell structures. Chemistry: A European Journal. ,vol. 10, pp. 2822- 2830 ,(2004) , 10.1002/CHEM.200305305
Yasuhiro Kubota, Kyosuke Satake, Ryusuke Ikui, Hideki Okamoto, Masaru Kimura, Nucleophilic Reactions of 5-tert-Butyl-2-methoxy-3H-azepine with Alkoxides and Alkyllithium Reagents Bulletin of the Chemical Society of Japan. ,vol. 76, pp. 805- 811 ,(2003) , 10.1246/BCSJ.76.805
Nobuhiro Kihara, Kazuyuki Kidoba, Dynamic covalent chemistry of the Nicholas ether-exchange reaction. Organic Letters. ,vol. 11, pp. 1313- 1316 ,(2009) , 10.1021/OL900095D
Elena Stanoeva, Weidong He, Maria Teresa Rocchetti, Tuyen Nguyen Van, Norbert De Kimpe, None, Synthesis of 1-substituted 2,9,10-trioxatricyclo[4.3.1.03,8]decanes Tetrahedron. ,vol. 60, pp. 5077- 5084 ,(2004) , 10.1016/J.TET.2004.04.016