Synthesis of cholesteryl-α-d-lactoside via generation and trapping of a stable β-lactosyl iodide
作者： Ryan A. Davis , James C. Fettinger , Jacquelyn Gervay-Hague
DOI: 10.1016/J.TETLET.2015.05.012
关键词:
摘要: The generation of β-lactosyl iodide was carried out under non-in situ-anomerization, metal free conditions by reacting commercially available β-per-O-acetylated lactose with trimethylsilyl (TMSI). β-iodide surprisingly stable as evidenced NMR spectroscopy. Introduction octanol or cholesterol microwave gave high yields α-linked glycoconjugates. Careful analysis the reaction products and mechanistic considerations suggest an acid catalyzed rearrangement that provides glycosylation a C2-hydroxyl. Accessibility to these compounds may further advance glycolipidomic profiling immune modulating bacterial derived-glycans.
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sci-hub.se 参考文章(30)
R. U. Lemieux, H. Driguez, Chemical synthesis of 2-O-(.alpha.-L-fucopyranosyl)-3-O-(.alpha.-D-galactopyranosyl)-D-galactose. Terminal structure of the blood-group B antigenic determinant Journal of the American Chemical Society. ,vol. 97, pp. 4069- 4075 ,(1975) , 10.1021/JA00847A034
Joseph B. Lambert, Sol M. Ciro, The Interaction of π Orbitals with a Carbocation over Three σ Bonds Journal of Organic Chemistry. ,vol. 61, pp. 1940- 1945 ,(1996) , 10.1021/JO951643D
Sophon Kaeothip, Jagodige P. Yasomanee, Alexei V. Demchenko, Glycosidation of thioglycosides in the presence of bromine: mechanism, reactivity, and stereoselectivity. Journal of Organic Chemistry. ,vol. 77, pp. 291- 299 ,(2012) , 10.1021/JO2019174
J. Broome, B. R. Brown, G. H. R. Summers, 397. A new preparation of steroid halides Journal of the Chemical Society (Resumed). pp. 2071- 2073 ,(1957) , 10.1039/JR9570002071
Jacquelyn Gervay, Truc N. Nguyen, Michael J. Hadd, Mechanistic studies on the stereoselective formation of glycosyl iodides: first characterization of β-d-glycosyl iodides Carbohydrate Research. ,vol. 300, pp. 119- 125 ,(1997) , 10.1016/S0008-6215(96)00321-7
Daniel K. Baeschlin, André R. Chaperon, Virginie Charbonneau, Luke G. Green, Steven V. Ley, Ulrich Lücking, Eric Walther, Rapid Assembly of Oligosaccharides: Total Synthesis of a Glycosylphosphatidylinositol Anchor ofTrypanosoma brucei Angewandte Chemie International Edition. ,vol. 37, pp. 3423- 3428 ,(1998) , 10.1002/(SICI)1521-3773(19981231)37:24<3423::AID-ANIE3423>3.0.CO;2-I
Ryan A. Davis, Chun-Hung Lin, Jacquelyn Gervay-Hague, Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside: a product of host cholesterol efflux promoted by Helicobacter pylori. Chemical Communications. ,vol. 48, pp. 9083- 9085 ,(2012) , 10.1039/C2CC33948J
R. U. Lemieux, K. B. Hendriks, R. V. Stick, K. James, Halide ion catalyzed glycosidation reactions. Syntheses of .alpha.-linked disaccharides Journal of the American Chemical Society. ,vol. 97, pp. 4056- 4062 ,(1975) , 10.1021/JA00847A032
Anatoly Chernyak, Stefan Oscarson, Dominika Turek, Synthesis of the Lewis b hexasaccharide and squarate acid-HSA conjugates thereof with various saccharide loadings. Carbohydrate Research. ,vol. 329, pp. 309- 316 ,(2000) , 10.1016/S0008-6215(00)00189-0
Teiichi Murakami, Yukari Sato, Motonari Shibakami, Stereoselective glycosylations using benzoylated glucosyl halides with inexpensive promoters Carbohydrate Research. ,vol. 343, pp. 1297- 1308 ,(2008) , 10.1016/J.CARRES.2008.03.019