Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline
Status PubMed-not-MEDLINE Jazyk angličtina Země Německo Médium print-electronic
Typ dokumentu časopisecké články
PubMed
22509213
PubMed Central
PMC3326621
DOI
10.3762/bjoc.8.48
Knihovny.cz E-zdroje
- Klíčová slova
- glycosidase, glycosylation, nitrophenyl, oxazoline, α-ManNAc,
- Publikační typ
- časopisecké články MeSH
The synthetic procedures for a large-scale preparation of o- and p-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside are described. The synthetic pathway employs the glycosylation of phenol with ManNAc oxazoline, followed by nitration of the aromatic moiety yielding a separable mixture of the o- and p-nitrophenyl derivative in a 2:3 ratio.
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Krist P, Herkommerová-Rajnochová E, Rauvolfová J, Semeňuk T, Vavrušková P, Pavlíček J, Bezouška K, Petruš L, Křen V. Biochem Biophys Res Commun. 2001;287:11–20. doi: 10.1006/bbrc.2001.5537. PubMed DOI
Sedmera P, Přikrylová V, Bezouška K, Rajnochová E, Thiem J, Křen V. J Carbohydr Chem. 1998;17:1351–1357. doi: 10.1080/07328309808002358. DOI
Attolino E, Bonaccorsi F, Catelani G, D'Andrea F, Křenek K, Bezouška K, Křen V. J Carbohydr Chem. 2008;27:156–171. doi: 10.1080/07328300802030845. DOI
Lee C J, Fraser B A. J Biol Chem. 1980;255:6847–6853. PubMed
Lee C J, Banks S D, Li J P. Crit Rev Microbiol. 1991;18:89–114. doi: 10.3109/10408419109113510. PubMed DOI
Yoshimura J, Sakai H, Oda N, Hashimoto H. Bull Chem Soc Jpn. 1972;45:2027–2031. doi: 10.1246/bcsj.45.2027. DOI
Krist P, Kuzma M, Pelyvás I F, Simerská P, Křen V. Collect Czech Chem Commun. 2003;68:801–811. doi: 10.1135/cccc20030801. DOI
Popelová A, Kefurt K, Hlaváčková M, Moravcová J. Carbohydr Res. 2005;340:161–166. doi: 10.1016/j.carres.2004.11.002. PubMed DOI
Rich J R, Withers S G. Nat Chem Biol. 2009;5:206–215. doi: 10.1038/nchembio.148. PubMed DOI
Hollósi M, Kollát E, Laczkó I, Medzihradsky K F, Thurin J, Otvös L., Jr Tetrahedron Lett. 1991;32:1531–1534. doi: 10.1016/S0040-4039(00)74264-X. DOI
Lopin C, Jacquinet J-C. Angew Chem, Int Ed. 2006;45:2574–2578. doi: 10.1002/anie.200503551. PubMed DOI
Wittmann V, Lennartz D. Eur J Org Chem. 2002:1363–1367. doi: 10.1002/1099-0690(200204)2002:8<1363::AID-EJOC1363>3.0.CO;2-#. DOI
Heidlas J E, Lees W J, Pale P, Whitesides G M. J Org Chem. 1992;57:146–151. doi: 10.1021/jo00027a028. DOI
Freese S J, Vann W F. Carbohydr Res. 1996;281:313–319. doi: 10.1016/0008-6215(95)00345-2. DOI
Subramanian V, Moume-Pymbock M, Hu T, Crich D. J Org Chem. 2011;76:3691–3709. doi: 10.1021/jo102411j. PubMed DOI PMC
Weissmann B. J Org Chem. 1966;31:2505–2509. doi: 10.1021/jo01346a018. PubMed DOI
Bock K, Pedersen C. J Chem Soc, Perkin Trans 2. 1974:293–297. doi: 10.1039/P29740000293. DOI
Yamayaki T, Warden C H, Herscovics A, Jeanloz R W. Carbohydr Res. 1980;79:C9–C12. doi: 10.1016/S0008-6215(00)85143-5. DOI