A practical and scalable process to selectively monofunctionalize water-soluble α,ω-diols

作者: Quanxuan Zhang , Hong Ren , Gregory L. Baker

DOI: 10.1016/J.TETLET.2014.04.066

关键词:

摘要: Abstract A practical protocol for rapid and scalable synthesis of monofunctionalized α,ω-diols using a simple inexpensive THP ether protection/deprotection strategy was described. Use DHP source ease to remove excess water-soluble after deprotection render the process scale-friendly without need column chromatographic separation. The application present method also illustrated in preparation heterobifunctional diols well-defined extended oligo(ethylene glycol).

参考文章(23)
Abderrahim Bouzide, Gilles Sauvé, Highly selective silver(I) oxide mediated monoprotection of symmetrical diols Tetrahedron Letters. ,vol. 38, pp. 5945- 5948 ,(1997) , 10.1016/S0040-4039(97)01328-2
François A. Loiseau, King Kuok (Mimi) Hii, Alison M. Hill, Multigram synthesis of well-defined extended bifunctional polyethylene glycol (PEG) chains. Journal of Organic Chemistry. ,vol. 69, pp. 639- 647 ,(2004) , 10.1021/JO035042V
Daniel Raederstorff, Arthur Y. L. Shu, Janice E. Thompson, Carl Djerassi, Biosynthetic studies of marine lipids. 11. Synthesis, biosynthesis, and absolute configuration of the internally branched demospongic acid, 22-methyl-5,9-octacosadienoic acid Journal of Organic Chemistry. ,vol. 52, pp. 2337- 2346 ,(1987) , 10.1021/JO00388A001
Sofia Svedhem, Carl-Åke Hollander, Jing Shi, Peter Konradsson, Bo Liedberg, Stefan C. T. Svensson, Synthesis of a series of oligo(ethylene glycol)-terminated alkanethiol amides designed to address structure and stability of biosensing interfaces Journal of Organic Chemistry. ,vol. 66, pp. 4494- 4503 ,(2001) , 10.1021/JO0012290
Yiyan Chen, Gregory L. Baker, Synthesis and Properties of ABA Amphiphiles. Journal of Organic Chemistry. ,vol. 64, pp. 6870- 6873 ,(1999) , 10.1021/JO990620M
Dan Niculescu-Duvaz, Jayne Getaz, Caroline J. Springer, Long functionalized poly(ethylene glycol)s of defined molecular weight: synthesis and application in solid-phase synthesis of conjugates. Bioconjugate Chemistry. ,vol. 19, pp. 973- 981 ,(2008) , 10.1021/BC060242+
Takeshi Nishiguchi, Shizuo Fujisaki, Yasuhiro Ishii, Yoshihiro Yano, Akiko Nishida, Convenient Selective Monoacylation of 1,n-Diols Catalyzed by Ion-Exchange Resins Journal of Organic Chemistry. ,vol. 59, pp. 1191- 1195 ,(1994) , 10.1021/JO00084A043
Saleh A. Ahmed, Mutsuo Tanaka, Synthesis of oligo(ethylene glycol) toward 44-mer. Journal of Organic Chemistry. ,vol. 71, pp. 9884- 9886 ,(2006) , 10.1021/JO0617464
David O. Johnston, The methanolysis of acetal: a chemical kinetics and gas chromatography experiment Journal of Chemical Education. ,vol. 44, pp. 33- ,(1967) , 10.1021/ED044P33