Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2006(10): 1645-1651
DOI: 10.1055/s-2006-926447
DOI: 10.1055/s-2006-926447
PAPER
© Georg Thieme Verlag Stuttgart · New York
Ionic-Tag-Assisted Oligosaccharide Synthesis
Further Information
Received
20 November 2005
Publication Date:
21 April 2006 (online)
Publication History
Publication Date:
21 April 2006 (online)
![](https://www.thieme-connect.de/media/synthesis/200610/lookinside/thumbnails/10.1055-s-2006-926447-1.jpg)
Abstract
A new strategy to synthesize oligosaccharides by using ionic liquid as a tag has been demonstrated. This approach provides a way to construct oligosaccharides with greatly simplified purification, requiring no chromatography during the synthesis or at the end of cleavage of the tag.
Key words
oligosaccharides - solution-phase synthesis - ionic liquid
- 1 For a recent example of outstanding achievement in solution-phase synthesis of oligosaccharide, see:
Dudkin VY.Miller JS.Danishefsky SJ. J. Am. Chem. Soc. 2004, 126: 736 - 2
Seeberger PH.Danishefsky SJ. Acc. Chem. Res. 1998, 31: 685 - 3
Plante OJ.Palmacci ER.Seeberger PH. Science 2001, 291: 1523 - 4
Sears P.Wong C.-H. Science 2001, 291: 2344 - 5
Jaunzems J.Hofer E.Jesberger M.Sourkouni-Argirusi G.Kirschning A. Angew. Chem. Int. Ed. 2003, 42: 1166 -
6a
Seeberger PH.Haase WC. Chem. Rev. 2000, 100: 4349 -
6b
Osborn HMI.Khan TH. Tetrahedron 1999, 55: 1807 - 7
Love KR.Seeberger PH. Angew. Chem. Int. Ed. 2004, 43: 602 -
8a
Douglas SP.Whitfield DM.Krepinsky JJ. J. Am. Chem. Soc. 1991, 113: 5095 -
8b
Douglas SP.Whitfield DM.Krepinsky JJ. J. Am. Chem. Soc. 1995, 117: 2116 - 9
Jiang L.Hartly RC.Chan T.-H. Chem. Commun. 1996, 2193 - 10
Ito Y.Ogawa T. J. Am. Chem. Soc. 1997, 119: 5562 - 11
Wentworth P.Janda KD. Chem. Commun. 1999, 1918 - 12
Majumdar D.Zhu T.Boons G.-J. Org. Lett. 2003, 5: 3591 -
13a
Horváth IT.Rábai J. Science 1994, 266: 72 -
13b
Studer A.Hadida S.Ferritto SY.Kim PY.Jeger P.Wipf P.Curran DP. Science 1997, 275: 823 - For review, see:
-
13c
Zhang W. Tetrahedron 2003, 59: 4475 -
14a
Curran DP.Ferrito R.Hua Y. Tetrahedron Lett. 1998, 39: 4937 -
14b
Miura T.Goto K.Hosaka D.Inazu T. Angew. Chem. Int. Ed. 2003, 42: 2047 -
14c
Miura T.Hirose Y.Ohmae M.Inazu T. Org. Lett. 2001, 3: 3947 -
14d
Miura T.Inazu T. Tetrahedron Lett. 2003, 44: 1819 -
14e
Jing Y.Huang X. Tetrahedron Lett. 2004, 45: 4615 -
14f
Manzoni L. Chem. Commun. 2003, 2930 -
14g
Manzoni L.Castelli R. Org. Lett. 2004, 6: 4195 -
14h
Palmacci ER.Hewitt MC.Seeberger PH. Angew. Chem. Int. Ed. 2001, 40: 4433 - 15
Mizuno M.Goto K.Miura T.Matsuura T.Inazu T. Tetrahedron Lett. 2004, 45: 3425 - For recent reviews on ionic liquids, see:
-
16a
Wasserscheid P.Keim W. Angew. Chem. Int. Ed. 2000, 39: 3773 -
16b
Welton T. Chem. Rev. 1999, 99: 2071 -
16c
Sheldon R. Chem. Commun. 2001, 2399 -
16d
Wilkes JS. Green Chem. 2002, 4: 73 -
16e
Wasserscheid P.Welton T. Ionic Liquids in Synthesis Wiley-VCH; Weinheim: 2003. -
17a
Miao W.Chan TH. Org. Lett. 2003, 5: 5003 -
17b
Fraga-Dubreuil J.Bazureau JP. Tetrahedron 2003, 59: 6121 - 18
Miao W.Chan TH. J. Org. Chem. 2005, 70: 3251 - 19
Jiang L.Chan TH. J. Org. Chem. 1998, 63: 6035 -
20a
Kahne D.Walker S.Cheng Y.Van Eugen D. J. Am. Chem. Soc. 1989, 111: 6881 -
20b
Yan L.Kahne D. J. Am. Chem. Soc. 1996, 118: 9239 -
20c
Gildersleeve J.Pascal RA.Kahne D. J. Am. Chem. Soc 1998, 120: 5961 -
20d
Gildersleeve J.Smith A.Sakurai K.Raghavan S.Kahne D. J. Am. Chem. Soc. 1999, 121: 6176 -
20e
Liang R.Yan L.Leobach J.Ge M.Uozumi Y.Sekanina K.Horan N.Gildersleeve J.Thompson C.Smith A.Biswas K.Still WC.Kahne D. Science 1996, 274: 1520 -
21a
Crich D.Sun S. J. Org. Chem. 1997, 62: 198 -
21b
Crich D.Smith M. J. Am. Chem. Soc. 2002, 124: 8867 -
21c
Crich D.de la Mora M.Vinod AU. J. Org. Chem. 2003, 68: 8142 -
22a
Garcia B.Poole JL.Gin DY. J. Am. Chem. Soc. 1997, 119: 7597 -
22b
Honda E.Gin DY. J. Am. Chem. Soc. 2002, 124: 7342 -
22c
Wipf P.Reeves JT. J. Org. Chem. 2001, 66: 7910 - 23
Guillier F.Orain D.Bradley M. Chem. Rev. 2000, 100: 2091