Step-economy synthesis of β-steryl sialosides utilizing a sialyl iodide donor


Davis RA, Lin C-H, Gervay-Hague J. Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-[small alpha]-d-glucopyranoside: a product of host ldl cholesterol efflux promoted by Helicobacter pylori. Chem Commun. 2012;48:9083–5.


Davis RA, Fettinger JC, Gervay-Hague J. Tandem glycosyl iodide glycosylation and regioselective enzymatic acylation affords 6-O-tetradecanoyl-α-d-cholesterylglycosides. J Org Chem. 2014;79:8447–52.


Nguyen HQ, Davis RA, Gervay-Hague J. Synthesis and structural characterization of three distinctive Helicobacter pylori α-cholesteryl phosphatidyl glucosides. Angew Chem Int Ed. 2014;126:1–5.


Jan H-M, et al. Metabolic labelling of cholesteryl glucosides in Helicobacter pylori reveals how the uptake of human lipids enhances bacterial virulence. Chem Sci. 2016;7:6208–16.


Grille S, Zaslawski A, Thiele S, Plat J, Warnecke D. The features of steryl glycosides come to those that wait: Latest advances in vegetation, fungi, micro organism and animals. Prog Lipid Res. 2010;49:262–88.


Gervay-Hague J. Taming the reactivity of glycosyl iodides to realize stereoselective glycosidation. Acc Chem Res. 2015.


Danishefsky SJ, Deninno MP. The full synthesis of (+/-)-N-acetylneuraminic acid (Nana) – a exceptional hydroxylation of a (Z)-Enoate. J Org Chem. 1986;51:2615–7.


Traving C, Schauer R. Construction, perform and metabolism of sialic acids. Cell Mol Life Sci. 1998;54:1330–49.


Kiefel MJ, von Itzstein M. Latest advances within the synthesis of sialic acid derivatives and sialylmimetics as organic probes. Chem Rev. 2002;102:471–90.


Varki A. Glycan-based interactions involving vertebrate sialic-acid-recognizing proteins. Nature. 2007;446:1023–9.


Tanaka Y, Ando S. Modulation of cholinergic synaptic features by sialylcholesterol. Glycoconj J. 1996;13:321–6.


Veeneman GH, et al. Synthesis of sialic-acid lipid conjugates and their neuritogenic results on N1e.115 neuroblastoma-cells. Bioorg Med Chem Lett. 1995;5:9–14.


Crich D, Li W. Environment friendly glycosidation of a phenyl thiosialoside donor with diphenyl sulfoxide and triflic anhydride in dichloromethane. Org Lett. 2006;Eight:959–62.


Du YG, Linhardt RJ. Stereospecific synthesis of alpha-C-glycosyl derivatives (“alpha-C-glycosides”) of N-acetylneuraminic acid by samarium-mediated reductive desulfonylation of a glycosyl phenylsulfone. Carbohydr Res. 1998;308:161–four.


Gervay J, Gregar TQ. HI/acetic acid discount of peracetylated N-acetyl neuraminic acid esters to stereoselectively present alpha-2-deoxy-2-hydrido derivatives. Tetrahedron Lett. 1997;38:5921–four.


De Meo C, Priyadarshani U. C-5 modifications in N-acetyl-neuraminic acid: scope and limitations. Carbohydr Res. 2008;343:1540–52.


Gong J, Liu H, Nicholls JM, Li X. Research on the sialylation of galactoses with completely different C-5 modified sialyl donors. Carbohydr Res. 2012;361:91–9.


Demchenko AV, Boons GJ. A novel and versatile glycosyl donor for the preparation of glycosides of N-acetylneuraminic acid. Tetrahedron Lett. 1998;39:3065–Eight.


Kaupp M, Malkina OL, Malkin VG, Pyykko P. How do spin-orbit-induced heavy-atom results on NMR chemical shifts perform? Validation of a easy analogy to spin-spin coupling by density practical concept (DFT) calculations on some iodo compounds. Chem Eur J. 1998;four:118–26. 10.1002/(Sici)1521-3765(199801)four:13.Three.CO;2-Y.


Orlova AV, Shpirt AM, Kulikova NY, Kononov LO. N,N-Diacetylsialyl chloride-a novel readily accessible sialyl donor in reactions with impartial and charged nucleophiles within the absence of a promoter. Carbohydr Res. 2010;345:721–30.


Crich D, Li W. alpha-selective sialylations at -78 levels C in nitrile solvents with a 1-adamantanyl thiosialoside. J Org Chem. 2007;72:7794–7.


Farris MD, De Meo C. Software of four,5-O,N-oxazolidinone protected thiophenyl sialosyl donor to the synthesis of alpha-sialosides. Tetrahedron Lett. 2007;48:1225–7.


Tanaka H, Adachi M, Takahashi T. One-pot synthesis of sialo-containing glycosyl amino acids by use of an N-trichloroethoxycarbonyl-beta-thiophenyl sialoside. Chem Eur J. 2005;11:849–62.


Ikeda Ok, Miyamoto Ok, Sato M. Synthesis of N,N-Ac,Boc laurylthio sialoside and its utility to O-sialylation. Tetrahedron Lett. 2007;48:7431–5.


Harris BN, Patel PP, Gobble CP, Stark MJ, De Meo C. C-5 modified S-benzoxazolyl sialyl donors: in the direction of extra environment friendly selective sialylations. Eur J Org Chem. 2011:4023–7.


El-Badri MH, Willenbring D, Tantillo DJ, Gervay-Hague J. Mechanistic research on the stereoselective formation of beta-mannosides from mannosyl iodides utilizing alpha-deuterium kinetic isotope results. J Org Chem. 2007;72:4663–72.


Hsieh HW, Davis RA, Hoch JA, Gervay-Hague J. Two-step functionalization of oligosaccharides utilizing glycosyl iodide and trimethylene oxide and its functions to multivalent glycoconjugates. Chem Eur J. 2014;20:6444–54.


Boer DR, et al. Calculated heats of formation of sterol diene isomers in contrast with artificial yields of isomerisation reactions of Δ5,7 sterols. J Chem Soc, Perkin Trans. 2000;2:1701–four.


Dolle RE, Schmidt SJ, Eggleston D, Kruse LJ. Research on the acid-catalyzed homonuclear steroidal diene isomerization. J Org Chem. 1988;53:1563–6.


Houot F, Grasset L, Magnoux P, Amblès A. Catalytic transformation of ldl cholesterol over HFAU zeolites. J Mol Cat A Chem. 2007;265:117–26.


Liu R-M, Chillier XFD, Kamalaprija P, Burger U, Gulacar FO. Acid-catalysed spine rearrangement of cholesta-6,Eight(14)-dienes. Helv Chim Acta. 1996;79:989–98.


Wilson WK, Schroepfer GJ. Acid-catalyzed isomerization of 7-dehydrocholesterol benzoate. A revised mechanism and an improved artificial process. J Org Chem. 1988;53:1713–9.


Schombs M, Park FE, Du W, Kulkarni SS, Gervay-Hague J. One-pot syntheses of immunostimulatory glycolipids. J Org Chem. 2010;75:4891–Eight.


Kulkarni SS, Gervay-Hague J. Environment friendly synthesis of a C-analogue of the immunogenic bacterial glycolipid BbGL2. Org Lett. 2006;Eight:5765–Eight.


Tanaka SI, Goi T, Tanaka Ok, Fukase Ok. Extremely environment friendly alpha-sialylation by advantage of fastened dipole results of N-phthalyl group: utility to steady circulate synthesis of alpha(2-Three)- and alpha(2-6)-Neu5Ac-Gal motifs by microreactor. J Carbohyd Chem. 2007;26:369–94.


Jensen HH, Bols M. Stereoelectronic substituent results. Acc Chem Res. 2006;39:259–65.


Smith DM, Woerpel KA. Electrostatic interactions in cations and their significance in biology and chemistry. Org Biomol Chem. 2006;four:1195–201.


Sato S, et al. Synthesis of 2- (5-Cholesten-3β-yloxy) glycosides of N-acetyl-D-neuraminic acid derivatives. Chem Pharm Bull. 1987;35:4043–Eight.

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