63294-76-8Relevant academic research and scientific papers
A practical and scalable process to selectively monofunctionalize water-soluble α,ω-diols
Zhang, Quanxuan,Ren, Hong,Baker, Gregory L.
supporting information, p. 3384 - 3386 (2014/06/09)
A practical protocol for rapid and scalable synthesis of monofunctionalized α,ω-diols using a simple and inexpensive THP ether protection/deprotection strategy was described. Use of inexpensive DHP source and ease to remove excess water-soluble α,ω-diols
Z-selective intramolecular Horner-Wadsworth-Emmons reaction for the synthesis of macrocyclic alkenes
Ando, Kaori,Sato, Kaori
scheme or table, p. 1284 - 1287 (2011/03/22)
The Z-selective intramolecular Horner-Wadsworth-Emmons reaction of the substrates 7-12 (RO)2P(O)CHR′CO2Et (R′ = (CH2)nCHO) (R = Ph or o-tBuC6H4) gives the 13-18-membered cyclic alkenes selectively (up to Z:E = 97:3) in good yields using NaH in THF under high dilution conditions.
Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin, squamostolide, and their inhibitory action with bovine heart mitochondrial complex I
Makabe, Hidefumi,Kimura, Yuka,Higuchi, Masaharu,Konno, Hiroyuki,Murai, Masatoshi,Miyoshi, Hideto
, p. 3119 - 3130 (2007/10/03)
A convergent stereoselective synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin and squamostolide was accomplished via a Pd-catalyzed cross-coupling reaction. The inhibitory activity of these compounds was examined with bovine heart mitochondrial NADH-ubiquinone oxidoreductase. These compounds showed a remarkably weak inhibitory activity compared to ordinary acetogenins such as bullatacin. Our results indicate that to maintain potent inhibitory effect, the hydroxylated lactone cannot substitute for the hydroxylated mono- or bis-THF rings with a long alkyl chain that can be seen in ordinary acetogenins.
A mild and efficient selective tetrahydropyranylation of primary alcohols and deprotection of THP ethers of phenols and alcohols using PdCl 2(CH3CN)2 as catalyst
Wang, Yan-Guang,Wu, Xiao-Xing,Jiang, Zhi-Yong
, p. 2973 - 2976 (2007/10/03)
Primary alcohols were selectively tetrahydropyranylated in good to excellent yields at room temperature using PdCl2(CH 3CN)2 as catalyst in tetrahydrofuran (THF) in the presence of phenols, secondary, and tertiary alcohols. The tetrahydropyranyl (THP) group could be efficiently removed using PdCl2(CH 3CN)2 as catalyst in CH3CN, while other protection groups such as p-toluenesulfonyl (Ts), tert-butyldiphenylsilyl (TBDPS), benzyloxycarbonyl (Cbz), allyl, benzyl (Bn), and benzoyl (Bz) remained intact under these conditions.
