Stereoselective glycosylation with conformation-constrained 2-Nitroglycals as donors and bifunctional thiourea as catalyst

References

• (a) Gandhi, N. S.; Mancera, R. L. The structure of glycosaminoglycans and their interactions with proteins. Chem Biol Drug Des. 2008, 72(6), 455–482. DOI: https://doi.org/10.1111/j.1747-0285.2008.00741.x.
   PubMed Web of Science ®Google Scholar
  (b) Hainrichson, M.; Nudelman, I.; Baasov, T. Designer aminoglycosides: the race to develop improved antibiotics and compounds for the treatment of human genetic diseases. Org. Biomol. Chem. 2008, 6(2), 227–239. DOI: https://doi.org/10.1039/b712690p.
   PubMed Web of Science ®Google Scholar
  (c) Kumar, S.; Xue, L.; Arya, D. P. Neomycin-neomycin dimer: an all-carbohydrate scaffold with high affinity for AT-rich DNA duplexes. J. Am. Chem. Soc. 2011, 133(19), 7361–7375. DOI: https://doi.org/10.1021/ja108118v.
   PubMed Web of Science ®Google Scholar
  (d) Huo; X, C.; Ye, X. S. Recent advance in carbohydrate-based cancer vaccines. Acta. Pharm. Sin 2012, 47, 261–270.
   Google Scholar
  (e) Jaurigue, J. A.; Seeberger, P. H. Parasite carbohydrate vaccines. Front. Cell. Infect. Microbiol. 2017, 7, 248. DOI: https://doi.org/10.3389/fcimb.2017.00248.
   PubMed Web of Science ®Google Scholar
  (f) Micoli, F.; Costantino, P.; Adamo, R. Potential targets for next generation antimicrobial glycoconjugate vaccines. FEMS Microbiol. Rev. 2018, 42(3), 388–423.
   PubMed Web of Science ®Google Scholar
• Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Synthesis of glycopeptides containing carbohydrate and peptide recognition motifs. Chem. Rev. 2000, 100(12), 4495–4538.
   PubMed Web of Science ®Google Scholar
• Lemieux, R. U.; Ratcliffe, R. M. The azidonitration of tri-O-acetyl-d-galactal. Can. J. Chem. 1979, 57(10), 1244–1251. DOI: https://doi.org/10.1139/v79-203.
   Web of Science ®Google Scholar
• (a) Schmidt, R. R.; Vankar, Y. D. 2-Nitroglycals as powerful glycosyl donors: application in the synthesis of biologically important molecules. Acc. Chem. Res. 2008, 41(8), 1059–1073. DOI: https://doi.org/10.1021/ar7002495.
   PubMed Web of Science ®Google Scholar
  (b) Delaunay, T.; Poisson, T.; Jubault, P.; Pannecoucke, X. 2-Nitroglycals: versatile building blocks for the synthesis of 2-aminoglycosides. Eur. J. Org. Chem. 2014, 2014(34), 7525–7546. DOI: https://doi.org/10.1002/ejoc.201402805.
   Web of Science ®Google Scholar
• Ngoje, G.; Li, Z. Study of the stereoselectivity of 2-azido-2-deoxyglucosyl donors: protecting group effects. Org. Biomol. Chem. 2013, 11(11), 1879–1886.
   PubMed Web of Science ®Google Scholar
• Pal, K. B.; Guo, A.; Das, M.; Báti, G.; Liu, X. W. Superbase-catalyzed stereo- and regioselective glycosylation with 2-nitroglycals: Facile access to 2-amino-2-deoxy-O-glycosides. ACS Catal. 2020, 10(12), 6707–6715. DOI: https://doi.org/10.1021/acscatal.0c00753.
   Web of Science ®Google Scholar
• (a) Medina, S.; Harper, M. J.; Balmond, E. I.; Miranda, S.; Crisenza, G. E.; Coe, D. M.; McGarrigle, E. M.; Galan, M. C. Stereoselective glycosylation of 2-Nitrogalactals catalyzed by a bifunctional organocatalyst. Org. Lett. 2016, 18(17), 4222–4225. DOI: https://doi.org/10.1021/acs.orglett.6b01962.
   PubMed Web of Science ®Google Scholar
  (b) Liu, J.-L.; Zhang, Y.-T.; Liu, H.-F.; Zhou, L.; Chen, J. N-Heterocyclic carbene catalyzed stereoselective glycosylation of 2-nitrogalactals. Org. Lett. 2017, 19(19), 5272–5275. DOI: https://doi.org/10.1021/acs.orglett.7b02543.
   PubMed Web of Science ®Google Scholar
  (c) Yoshida, K.; Kanoko, Y.; Takao, K.-I. Kinetically controlled α-selective O-glycosylation of phenol derivatives using 2-nitroglycals by a bifunctional chiral thiourea catalyst. Asian J. Org. Chem. 2016, 5(10), 1230–1236. DOI: https://doi.org/10.1002/ajoc.201600307.
   Web of Science ®Google Scholar
• Frihed, T. G.; Bols, M.; Pedersen, C. M. Mechanisms of glycosylation reactions studied by low temperature NMR. Chem. Rev. 2015, 115(11), 4963–5013. DOI: https://doi.org/10.1021/cr500434x.
   PubMed Web of Science ®Google Scholar
• (a) Satoh, H.; Manabe, S. Design of chemical glycosyl donors: does changing ring conformation influence selectivity/reactivity? Chem. Soc. Rev. 2013, 42(10), 4297–4309. DOI: https://doi.org/10.1039/c3cs35457a.
   PubMed Web of Science ®Google Scholar
  (b) Benakli, K.; Zha, C.; Kerns, R. J. Oxazolidinone protected 2-amino-2-deoxy-D-glucose derivatives as versatile intermediates in stereoselective oligosaccharide synthesis and the formation of alpha-linked glycosides. J. Am. Chem. Soc. 2001, 123(38), 9461–9462. DOI: https://doi.org/10.1021/ja0162109.
   PubMed Web of Science ®Google Scholar
  (c) van den Bos, L. J.; Litjens, R. E. J. N.; van den Berg, R. J. B. H. N.; Overkleeft, H. S.; van der Marel, G. A. Preparation of 1-thio uronic acid lactones and their use in oligosaccharide synthesis. Org. Lett. 2005, 7(10), 2007–2010. DOI: https://doi.org/10.1021/ol050491y.
   PubMed Web of Science ®Google Scholar
  (d) Manabe, S.; Ishii, K.; Ito, Y. N-benzyl-2,3-oxazolidinone as a glycosyl donor for selective alpha-glycosylation and one-pot oligosaccharide synthesis involving 1,2-cis-glycosylation. J. Am. Chem. Soc. 2006, 128(33), 10666–10667. DOI: https://doi.org/10.1021/ja062531e.
   PubMed Web of Science ®Google Scholar
  (e) Tanaka, H.; Nishiura, Y.; Takahashi, T. Stereoselective synthesis of oligo-alpha-(2,8)-sialic acids. J. Am. Chem. Soc. 2006, 128(22), 7124–7125. DOI: https://doi.org/10.1021/ja0613613.
   PubMed Web of Science ®Google Scholar
  (f) Zhu, X.; Kawatkar, S.; Rao, Y.; Boons, G. J. Practical approach for the stereoselective introduction of beta-arabinofuranosides . J. Am. Chem. Soc. 2006, 128(36), 11948–11957. DOI: https://doi.org/10.1021/ja0629817.
   PubMed Web of Science ®Google Scholar
  (g) Crich, D. Mechanism of a chemical glycosylation reaction. Acc. Chem. Res. 2010, 43(8), 1144–1153. DOI: https://doi.org/10.1021/ar100035r.
   PubMed Web of Science ®Google Scholar
  (h) Christina, A. E.; van den Bos, L. J.; Overkleeft, H. S.; van der Marel, G. A.; Codée, J. D. C. Galacturonic acid lactones in the synthesis of all trisaccharide repeating units of the zwitterionic polysaccharide Sp1. J. Org. Chem. 2011, 76(6), 1692–1706. DOI: https://doi.org/10.1021/jo102363d.
   PubMed Web of Science ®Google Scholar
  (i) Elferink, H.; Mensink, R. A.; White, P. B.; Boltje, T. J. Stereoselective β-mannosylation by neighboring-group participation. Angew. Chem. Int. Ed. Engl. 2016, 55(37), 11217–11220. DOI: https://doi.org/10.1002/anie.201604358.
   PubMed Web of Science ®Google Scholar
  (j) Yagami, N.; Imamura, A. Stereodirecting effect of cyclic silyl protecting groups in chemical glycosylation. Ras. 2018, 6(0), 1–20. DOI: https://doi.org/10.7831/ras.6.1.
   Google Scholar
• (a) Imamura, A.; Ando, H.; Korogi, S.; Tanabe, G.; Muraoka, O.; Ishida, H.; Kiso, M. di-tert-Butylsilylene (DTBS) group-directed selective galactosylation unaffected by C-2 participating functionalities. Tetrahedron Lett 2003, 44(35), 6725–6728. DOI: https://doi.org/10.1016/S0040-4039(03)01647-2.
   Web of Science ®Google Scholar
  (b) Balmond, E. I.; Benito-Alifonso, D.; Coe, D. M.; Alder, R. W.; McGarrigle, E. M.; Galan, M. C. A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides. Angew. Chem. Int. Ed. Engl. 2014, 53(31), 8190–8194.
   PubMed Web of Science ®Google Scholar
• Das, J.; Schmidt, R. R. Convenient glycoside synthesis of amino sugars: Michael-type addition to 2-nitro-d-galactal. Eur. J. Org. Chem. 1998, 1998(8), 1609–1613. DOI: https://doi.org/10.1002/(SICI)1099-0690(199808)1998:8<1609::AID-EJOC1609>3.0.CO;2-1.
   Web of Science ®Google Scholar
• Giordano, M.; Iadonisi, A. Tin-mediated regioselective benzylation and allylation of polyols: applicability of a catalytic approach under solvent-free conditions. J. Org. Chem. 2014, 79(1), 213–222.
   PubMed Web of Science ®Google Scholar
• (a) Kancharla, P. K.; Reddy, Y. S.; Dharuman, S.; Vankar, Y. D. Acetyl chloride-silver nitrate-acetonitrile: a reagent system for the synthesis of 2-nitroglycals and 2-nitro-1-acetamido sugars from glycals. J. Org. Chem. 2011, 76(14), 5832–5837. DOI: https://doi.org/10.1021/jo200475h.
   PubMed Web of Science ®Google Scholar
  (b) Dharuman, S.; Gupta, P.; Kancharla, P. K.; Vankar, Y. D. Synthesis of 2-nitroglycals from glycals using the tetrabutylammonium nitrate-trifluoroacetic anhydride-triethylamine reagent system and base-catalyzed Ferrier rearrangement of acetylated 2-nitroglycals. J. Org. Chem. 2013, 78(17), 8442–8450.
   PubMed Web of Science ®Google Scholar
• (a) Xue, Y. Jiangxi Normal University Master Thesis, 2021. 20–27.
   Google Scholar
  (b) Reddy, G. S.; Corey, E. J. A useful method for the conversion of olefins to nitro olefins. Org. Lett. 2021, 23(9), 3399–3402.
   PubMed Web of Science ®Google Scholar
• (a) Wittkopp, A.; Schreiner, P. R. Metal-free, noncovalent catalysis of diels ± alder reactions by neutral hydrogen bond donors in organic solvents and in water. Chem. Eur. J. 2003, 9, 407-414. (b) Schreiner, P. R. Metal-free organocatalysis through explicit hydrogen bonding interactions. Chem. Soc. Rev. 2003, 32, 289–296.
   Google Scholar
• Schnorr, J. M.; van der Zwaag, D.; Walish, J. J.; Weizmann, Y.; Swager, T. M. Sensory arrays of covalently functionalized single-walled carbon nanotubes for explosive detection. Adv. Funct. Mater. 2013, 23(42), 5285–5291. DOI: https://doi.org/10.1002/adfm.201300131.
   Web of Science ®Google Scholar
• Kvaernø, L.; Ritter, T.; Werder, M.; Hauser, H.; Carreira, E. M. An in vitro assay for evaluation of small-molecule inhibitors of cholesterol absorption. Angew. Chem. Int. Ed. 2004, 43(35), 4653–4656. DOI: https://doi.org/10.1002/anie.200460348.
   PubMed Web of Science ®Google Scholar
• Sato, K-i.; Sakai, K.; Kojima, M.; Akai, S. The use of 2-O-propagyloxycarbonyl protecting group in the selective formation of 1,2-trans-glycosidic linkage. Tetrahedron Lett 2007, 48(25), 4423–4425. DOI: https://doi.org/10.1016/j.tetlet.2007.04.083.
   Web of Science ®Google Scholar
• Yang, J.; Fu, X.; Jia, Q.; Shen, J.; Biggins, J. B.; Jiang, J.; Zhao, J.; Schmidt, J. J.; Wang, P. G.; Thorson, J. S. Studies on the substrate specificity of Escherichia coli galactokinase. Org. Lett. 2003, 5(13), 2223–2226.
   PubMed Web of Science ®Google Scholar
• Hanaya, T.; Baba, H.; Toyota, H.; Yamamoto, H. Synthetic studies on pterin glycosides: the first synthesis of 2′-O-(α-D-glucopyranosyl)biopterin. Tetrahedron 2009, 65(38), 7989–7997. DOI: https://doi.org/10.1016/j.tet.2009.07.043.
   Web of Science ®Google Scholar