Synthesis of thiosaccharides employing the Pummerer rearrangement of tetrahydrothiopyran oxides

Tetrahedron

Volumn 60, Issue 32, 2004, Pages 6829-6851

  Fujita, Junji ^a   Matsuda, Hiroko ^a,c   Yamamoto, Kazunori ^a   Morii, Yasuharu ^a   Hashimoto, Masaru ^a   Okuno, Toshikatsu ^a   Hashimoto, Kimiko ^b  

^a HIROSAKI UNIVERSITY   (Japan)

^b KEIO UNIVERSITY   (Japan)

^c Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

Isomaltotriose analogue; Pummerer rearrangements; Reaction mechanism; Thiosaccharids

Indexed keywords

CARBOHYDRATE DERIVATIVE; OXIDE; PYRIDINE; SULFONIUM DERIVATIVE; THIOPYRAN DERIVATIVE; TRIFLUOROACETIC ACID;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; PRIORITY JOURNAL; PUMMERER REACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 3142704211     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.006     Document Type: Article

References (44)

1. Hashimoto H., Izumi M. Tetrahedron Lett. 34:1993;4949-4952
2. Hashimoto H., Kawanishi M., Yuasa H. Chem. Eur. J. 2:1996;556-560
3. Hashimoto H., Shimada K., Horito S. Tetrahedron Lett. 34:1993;4953-4956
4. Ibatullin F.M., Shabalin K.A., Janis J.V., Selivanov S.I. Tetrahedron Lett. 42:2001;4565-4567
5. Izumi M., Tsuruta O., Harayama S., Hashimoto H. J. Org. Chem. 62:1997;992-998
6. Mehta S., Andrews J.S., Johnston B.D., Svensson B., Pinto B.M. J. Am. Chem. Soc. 117:1995;9783-9790
7. Mehta S., Jordan K.L., Weimar T., Kreis U.C., Batchelor R.J., Einstein F.W.B., Pinto B.M. Tetrahedron: Asymmetry. 5:1994;2367-2396
8. Matsuda H., Ohara K., Morii Y., Hashimoto M., Miyairi K., Okuno T. Bioorg. Med. Chem. Lett. 13:2003;1063-1066
9. Ohara K., Matsuda H., Hashimoto M., Miyairi K., Okuno T. Chem. Lett. 2002;626-627
10. Matsuda H., Fujita J., Morii Y., Hashimoto M., Okuno T., Hashimoto K. Tetrahedron Lett. 44:2003;4089-4093
11. Matsumoto T., Shirahama H., Ichihara A., Shin H., Kagawa S., Sakan F., Matsumoto S., Nishida S. J. Am. Chem. Soc. 90:1968;3280-3281
12. Konno K., Hashimoto K., Ohfune Y., Shirahama H., Matsumoto T. J. Am. Chem. Soc. 110:1988;4807-4815
13. McCormick J.E., McElhinney R.S. J. Chem. Soc., Perkin Trans. 1. 1976;2533-2540
14. Oae S., Itoh O., Numata T., Yoshimura T. Bull. Chem. Soc. Jpn. 56:1983;270-279
15. Oae S., Numata T. Buncel E., Lee C.C. Isotopes in Cationic Reactions. Vol. 5:1980;45-102 Elsevier, Oxford
16. Crucianelli M., Bravo P., Arnone A., Corradi E., Meille S.V., Zanda M. J. Org. Chem. 65:2000;2965-2971
17. Naka T., Minakawa N., Abe H., Kaga D., Matsuda A. J. Am. Chem. Soc. 122:2000;7233-7243
18. Naka T., Nishizono N., Minakawa N., Matsuda A. Tetrahedron Lett. 40:1999;6297-6300
19. Zhang X., Qing F.-L. J. Org. Chem. 67:2002;1016-1019
20. Merrer Y.L., Dureault A., Greck C., Micas-Languin D., Gravier C., Depezay J.-C. Heterocycles. 25:1987;541-548
21. Merrer Y.L., Fuzier M., Dosbaa I., Foglietti M.-J., Depezay J.-C. Tetrahedron. 53:1997;16731-16746
22. Brunet E., Eliel E.L. J. Org. Chem. 51:1986;677-686
23. Cahill R., Cookson R.C., Crabb T.A. Tetrahedron. 25:1969;4711-4735
24. 1H NMR spectrum clearly divided into two groups, the ax- and eq-sulfoxide groups. The coupling constants between C5H and both of the C6 methylene protons in the equatorial sulfoxides eq-9-12 were 2.5-5.4 Hz, which suggests that the relationship between H5 and H6 and H6′ of the equatorial isomers were both gauche, that is the conformation about the C5-C6 bond is gg. In contrast, the sizes of the coupling constants between H5 and one of the two H6s for the corresponding axial sulfoxides of 9-12 were large (9.3-11.7 Hz), indicating that these protons had an anti relationship. It appears that the potential 1, 3-diaxial relationship with the equatorial oxygen atom O-4 causes the tg conformation be of high energy and similarly the potential 1, 3-diaxial relationship with the axial sulfoxide oxygen atom causes the gg conformation be of high energy. Thus, the axial sulfoxides of 9-12 adopt the tg conformations about the C5-C6 bond almost exclusively, as shown
25. Buck K.W., Foster A.B., Pardoe W.D., Qadir M.H., Webber J.M. J. Chem. Soc., Chem. Commun. 1966;759-761
26. Foster A.B., Inch T.D., Qadir M.H., Webber J.M. J. Chem. Soc., Chem. Commun. 1968;1086-1089
27. Spartan 04 ver. 1.00 by Wavefunction Inc (18401 Von Karman Avenue, Suite 370, Irvine, CA 92612, USA) was used for the calculations
28. Hariharan P.C., Pople J.A. Chem. Phys. Lett., 66:1972;217
29. Horner L., Kaiser P. Ann. 19:1959;626
30. Driguez H., Henrissat B. Tetrahedron Lett. 22:1981;5061-5062
31. PC Spartan Pro ver.1.08 by Wavefunction Inc (18401 Von Karman Avenue, Suite 370, Irvine, CA 92612, USA) was used for the calculations
32. Dess D.B., Martin J.C. J. Org. Chem. 48:1983;4155-4156
33. Rucker G., Horster H., Gajwski W. Synth. Commun. 10:1980;623
34. Nakata T., Tanaka T., Oishi T. Tetrahedron Lett. 29:1981;4139
35. Yamazaki N., Kibayashi C. J. Am. Chem. Soc. 111:1989;1396-1408
36. Mitsunobu O., Yamada M. Bull. Chem. Soc. Jpn. 40:1967;2380
37. Very small differences were observed in the chemical shifts for the C1Hax (Δδ 0.012 ppm), the remained C6H (Δδ 0.018 ppm), and C2H (Δδ 0.009 ppm) due to the isotope effect as shown in Figure 3 of the text
38. Tvaroska I., Carver J.P. J. Phys. Chem. B. 101:1997;2992-2999
39. Elliot J., Warren S. Tetrahedron Lett. 27:1986;645-648
40. Oae S., Numata T. Tetrahedron Lett. 1977;1337
41. Stridsberg B., Allenmark S. Acta Chem. Scand. 28:1974;596
42. Izumi M., Suhara Y., Ichikawa Y. J. Org. Chem. 63:1998;4811-4816
43. Schmidt R.R., Jung K.-H. Hanessian S. Preparative Carbohydrate Chemistry. 1997;283-312 Marcel Dekker, New York
44. Oikawa Y., Yoshioka T., Yonemitsu O. Tetrahedron Lett. 23:1982;885