Dehydrative glycosylation with the Hendrickson reagent

Journal of Organic Chemistry

Volumn 76, Issue 21, 2011, Pages 9122-9126

  Mossotti, Matteo ^a   Panza, Luigi ^a  

^a UNIVERSITY OF EASTERN PIEDMONT   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANOMERICS;

GLYCOSYLATION; REACTION INTERMEDIATES; RESONANCE;

ESTERIFICATION;

HENDRICKSON REAGENT; OXYGEN 18; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DEHYDRATIVE GLYCOSYLATION; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE;

GLYCOSIDES; GLYCOSYLATION; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 80055088589     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2015856     Document Type: Article

References (27)

1. Dwek, R. A. Chem. Rev. 1996, 96, 683-720
2. Zhu, X.; Schmidt, R. R. Angew. Chem., Int. Ed. 2009, 48, 2-37
3. Garcia, B. A.; Gin, D. Y. J. Am. Chem. Soc. 2000, 122, 4269-4279 and references cited therein
4. Shingu, Y.; Miyachi, A.; Miura, Y.; Kobayashi, K.; Nishida, Y. Carbohydr. Res. 2004, 340, 2236-2244 and references cited therein
5. Hendrickson, J. B.; Hussoin, M. S. J. Org. Chem. 1989, 54, 1144-1149
6. Hendrickson, J. B.; Hussoin, M. S. J. Org. Chem. 1987, 52, 4137-4139
7. Xu, P.; Liu, G.-S.; Xi, J.; Wang, S.; Yao, Z.-J. Tetrahedron 2011, 67, 5455-5460
8. Moussa, Z.; Ahmed, S. A.; ElDouhaibi, A. S.; Al-Raqa, S. Y. Tetrahedron Lett. 2010, 51, 1826-1831
9. Elson, K. E.; Jenkins, I. D.; Loughlin, W. A. Org. Biomol. Chem. 2003, 1, 2958-2965
10. Mukaiyama, T.; Kobashi, Y. Chem. Lett. 2004, 33, 10-11
11. Mukaiyama, T.; Suda, S. Chem. Lett. 1990, 1143-1146
12. Quin, L. D. A Guide to Organophosphorous Chemistry; John Wiley and Sons: New York, 2000; Chapter 4, p 103.
13. Xiong, Q.; Wilson, W. K.; Pang, J. Lipids 2007, 42, 87-96
14. Kowalski, J.; Łotowski, Z.; Morzycki, J. W.; Płoszyń ska, J.; Sobkowiak, A.; Wilczewska, A. Z. Steroids 2008, 73, 543-548
15. Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734-753
16. For a related example, see ref 8. For a general discussion of the in situ anomerization, see, for example: Kulkami, S. S.; Gervay-Hague, J. In Handbook of Chemical Glycosylation; Demchenko, A. V., Ed.; Wiley-VCH: Berlin, 2008; Chapter 2, pp 71 and ff.
17. Crich, D.; Dyker, H. Tetrahedron Lett. 1989, 30, 475
18. Petersson, M. J.; Jenkins, I. D.; Loughlin, W. A. J. Org. Chem. 2008, 73, 4691-4693
19. 31P chemical shifts of alkoxyphosphonium salts that we measured are different from those reported in ref 10 for furanoses but are in agreement with the values usually reported in the literature. See, for example: Camp, D.; Jenkins, I. D. J. Org. Chem. 1989, 54, 3045
20. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925
21. Mereyala, H. B.; Reddy, G. V. Tetrahedron 1991, 47, 6435-6448
22. Shingu, Y.; Nishida, Y.; Dohi, H.; Kobayashi, K. Org. Biomol. Chem. 2003, 1, 2518-2521
23. Nishizawa, M.; Garcia, D. M.; Shin, T.; Yamada, H. Chem. Pharm. Bull. 1993, 41, 784-785
24. Hashimoto, S.; Honda, T.; Ikegami, S. Chem. Pharm. Bull. 1990, 38, 2323-2325
25. Bucher, C.; Gilmour, R. Angew. Chem., Int. Ed. 2010, 49, 8724-8728
26. Vankaylapati, H.; Singh, G.; Tranoy, I. Tetrahedron: Asymmetry 2001, 12, 1373-1381
27. Hirooka, M.; Koto, S. Bull. Chem. Soc. Jpn. 1998, 71, 2893-2902