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Synlett 2011(8): 1043-1046
DOI: 10.1055/s-0030-1259934
DOI: 10.1055/s-0030-1259934
SYNPACTS
© Georg Thieme Verlag
Stuttgart ˙ New York
Steering Glycosylation with the Carbon-Fluorine Bond
Further Information
Received
20 December 2010
Publication Date:
30 March 2011 (online)
Publication History
Publication Date:
30 March 2011 (online)
Abstract
2-Fluoroglycosyl donors display orthogonal stereoselectivities as a consequence of a reinforcing combination of the C-2-fluorine configuration and the inductive nature of the protecting groups.
Key words
charge-dipole interactions - fluorine - glycosides - glycosylations - oxonium ions
-
1a
Smart BE. J. Fluorine Chem. 2001, 109: 3 -
1b
O’Hagan D. Chem. Soc. Rev. 2008, 37: 308 - 2
Zechel DL.Withers SG. Acc. Chem. Res. 2000, 33: 11 - For selected examples of fluorinated glycostructures, see:
-
3a
Street IP.Armstrong CR.Withers SG. Biochemistry 1986, 25: 6021 -
3b
Burkart MD.Zhang Z.Hung S.-C.Wong C.-H. J. Am. Chem. Soc. 1997, 119: 11743 -
3c
Albert M.Paul BJ.Dax K. Synlett 1999, 1483 -
3d
Miyazaki T.Sakakibara T.Sato H.Kajihara Y. J. Am. Chem. Soc. 1999, 121: 1411 -
3e
Watts AG.Damager I.Amaya ML.Buschiazzo A.Alzari P.Frasch AC.Withers SG. J. Am. Chem. Soc. 2003, 125: 7532 -
3f
Tarling CA.Withers SG. Carbohydr. Res. 2004, 339: 2487 -
3g
Subramaniam V.Gurcha SS.Besra GS.Lowary TL. Bioorg. Med. Chem. 2005, 13: 1083 -
3h
Crich D.Li L. J. Org. Chem. 2007, 72: 1681 -
3i
Chokhawala HA.Cao H.Yu H.Chen X. J. Am. Chem. Soc. 2007, 129: 10630 -
3j
Benito D.Matheu MI.Morère A.Díaz Y.Castillón S. Tetrahedron 2008, 64: 10906 -
3k
Rempel BR.Withers SG. Aust. J. Chem. 2009, 62: 590 -
3l
Allman SA.Jensen HH.Vijayakrishnan B.Garnett JA.Leon E.Liu Y.Anthony DC.Sibson NR.Feizi T.Matthews S.Davis BG. ChemBioChem 2009, 10: 2522 -
3m
Boutureira O.D’Hooge F.Fernandez-Gonzalez M.Bernardes GJL.Sanchez-Navarro M.Koeppe JR.Davis BG. Chem. Commun. 2010, 46: 8142 -
3n
Hoffmann-Röder A.Kaiser A.Wagner S.Gaidzik N.Kowalczyk D.Westerlind U.Gerlitzki B.Schmitt E.Kunz H. Angew. Chem. Int. Ed. 2010, 49: 8498 -
3o
Wagner S.Mersch C.Hoffmann-Röder A. Chem. Eur. J. 2010, 16: 7319 -
3p See also the special edition ‘Fluoro
Sugars’: Carbohydr. Res.
2000,
327:
1
- 4
Kim HW.Rossi P.Shoemaker RK.DiMagno SG. J. Am. Chem. Soc. 1998, 120: 9082 - 5
Bresciani S.Lebl T.Slawin AMZ.O’Hagan D. Chem. Commun. 2010, 46: 5434 - 6
Withers SG.MacLennan DJ.Street IP. Carbohydr. Res. 1986, 154: 127 - 7
Adibekian A.Stallforth P.Hecht M.-L.Werz DB.Gagneux P.Seeberger PH. Chem. Sci. 2011, 2: 337 -
8a
Sun A.Lankin DC.Hardcastle K.Snyder JP. Chem. Eur. J. 2005, 11: 1579 - See also:
-
8b
Lankin DC.Chandrakumar NS.Rao SN.Spangler DP.Snyder JP. J. Am. Chem. Soc. 1993, 115: 3356 -
8c
Snyder JP.Chandrakumar NS.Sato H.Lankin DC. J. Am. Chem. Soc. 2000, 122: 544 -
8d
Lankin DC.Grunewald GL.Romero FA.Oren IY.Snyder JP. Org. Lett. 2002, 4: 3557 -
9a
Gooseman NE.O’Hagan D.Slawin AMZ.Teatle AM.Tozer DJ.Young RJ. Chem. Commun. (Cambridge) 2006, 3190 -
9b
Gooseman NEJ.O’Hagan D.Peach MJG.Slawin AMZ.Tozer DJ.Young RJ. Angew. Chem. Int. Ed. 2007, 119: 5904 - 10
Smith DM.Woerpel KA. Org. Biomol. Chem. 2006, 4: 1195 -
11a
Svansson L.Johnston BD.Gu J.-H.Patrick B.Pinto BM. J. Am. Chem. Soc. 2000, 122: 10769 -
11b
Szczepina MG.Johnston BD.Yuan Y.Svensson B.Pinto BM. J. Am. Chem. Soc. 2004, 126: 12458 -
12a
Antoinette J.Romero C.Tabacco SA.Woerpel KA. J. Am. Chem. Soc. 2000, 122: 168 -
12b
Ayala L.Lucero CG.Antionette J.Romero C.Tabacco SA.Woerpel KA. J. Am. Chem. Soc. 2003, 125: 15521 -
12c
Larsen CH.Ridgeway BH.Shaw JT.Smith DM.Woerpel KA. J. Am. Chem. Soc. 2005, 127: 10879 -
12d
Baghdasarian G.Woerpel KA. J. Org. Chem. 2006, 71: 6851 -
12e
Yang MT.Woerpel KA. J. Org. Chem. 2009, 74: 545 -
12f
Krumper JR.Salamant WA.Woerpel KA. J. Org. Chem. 2009, 74: 8039 - 13
Miljković M.Yeagley D.Deslongchamps P.Dory YL. J. Org. Chem. 1997, 62: 7597 -
14a
Marzabadi CH.Franck RW. Tetrahedron 2000, 56: 8385 -
14b
Hou D.Lowary TL. Carbohydr. Res. 2009, 344: 1911 - 15
Bucher C.Gilmour R. Angew. Chem. Int. Ed. 2010, 49: 8724 -
16a
Schmidt RR.Kinzy W. Adv. Carbohydr. Chem. Biochem. 1994, 50: 21 -
16b
Zhu X.Schmidt RR. Angew. Chem. Int. Ed. 2009, 48: 1900