Some Aspects of Selectivity in the Reaction of Glycosyl DonorsFootnote*

* Dedicated to the memory of Professor Jacques van Boom.

References

• Elie , C. J.J. , Verduyn , C. E. , Dreff , D. M. , Brounts , D. G.A. , van der Marel , G. A. and van Boom , J. H. 1990 . Synthesis of 6‐O‐(α‐D‐mannopyranosyl)‐D‐myo‐inositol: a fragment from Mycobacteria phospholipids . Tetrahedron , 46 : 8243 – 8254 .
   Web of Science ®Google Scholar
• Elie , C. J.J. , Verduyn , C. E. , Dreff , D. M. , Brounts , D. G.A. , van der Marel , G. A. and van Boom , J. H. 1992 . Iodonium ion‐mediated mannosylations of myo‐inositol: synthesis of mycobacteria phospholipid fragment . J. Carbohydr. Chem. , 11 : 715 – 739 .
   Web of Science ®Google Scholar
• Veeneman , G. H. and van Boom , J. H. 1990 . An efficient thioglycoside‐mediated formation of glycosidic linkages promoted by iodonium dicollidine perchlorate . Tetrahedron Lett. , 31 : 275 – 278 .
   Web of Science ®Google Scholar
• Veeneman , G. H. , van Leeuwen , S. H. and van Boom , J. H. 1990 . Iodonium ion promoted reactions at the anomeric centre II. An efficient thioglycoside mediated approach toward the formation of 1,2‐trans linked glycosides and glycosidic esters . Tetrahedron Lett. , 31 : 1331 – 1334 .
   Web of Science ®Google Scholar
• Trost , B. M. 1983 . Selectivity—a key to synthetic efficiency . Science , 219 : 245 – 250 .
   PubMed Web of Science ®Google Scholar
• Isbell , H. S. 1940 . Chemistry of the carbohydrates and glycoside . Ann. Rev. Biochem. , 9 : 65 – 92 .
   Google Scholar
• Frush , H. L. and Isbell , H. S. 1941 . Sugar acetates, acetylglycosyl halides and orthoacetates in relation to the Swalden inversion . J. Res. NBS , 27 : 413
   Google Scholar
• Winstein , S. W. and Buckles , R. E. 1942 . The role of neighboring groups in replacement reactions I. Retention of configuration in the reaction of some dihalides and acetoxyhalides with silver acetate . J. Am. Chem Soc. , 64 : 2780 – 2786 .
   Web of Science ®Google Scholar
• Capon , B. and McManus , S. P. 1976 . Neighboring Group Participation New York : Plenum .
   Google Scholar
• Crich , D. , Li , W. and Li , H. 2004 . Direct chemical synthesis of the β‐mannans: linear and block syntheses of the alternating β‐(13)‐β‐(14)‐mannan common to Rhodotorula glutinis, Rhodotorula mucilaginosa, and Leptospira biflexa . J. Am. Chem. Soc. , 126 : 15081 – 15086 . For an example involving benzylidene rings see
   PubMed Web of Science ®Google Scholar
• Spijker , N. M. and van Boeckel , C. A.A. 1991 . Double stereodifferentiation in carbohydrate coupling reactions: the mismatched interaction of donor and acceptor as an unprecedented factor governing the α/β ratio of glycoside formation . Angew. Chem. Int. Ed. Engl. , 30 : 180 – 183 .
   Web of Science ®Google Scholar
• Masamune , S. , Choy , W. , Petersen , J. S. and Sita , L. R. 1985 . Double asymmetric synthesis and a new strategy for stereochemical dontrol in organic synthesis . Angew. Chem. Int. Ed. Engl. , 24 : 1 – 30 .
   Web of Science ®Google Scholar
• Paulsen , H. 1984 . Selectivity a Goal for Synthetic Efficiency Edited by: Bartmann , W. and Trost , B. M.
   Google Scholar
• Paulsen , H. 1982 . Advances in selective chemical syntheses of complex oligosaccharides . Angew. Chem. Int. Ed. Engl. , 21 : 155 – 173 .
   Web of Science ®Google Scholar
• Paulsen , H. , Richter , A. , Sinnwell , V. and Stenzel , W. 1978 . Darstellung selektiv blockierter 2‐azido‐2‐desoxy‐D‐gluco‐ und ‐D‐galactopyranosylhalogenide: Reaktivität und 13C‐NMR‐spektren . Carbohydr. Res. , 64 : 339 – 362 .
   Web of Science ®Google Scholar
• Anilkumar , G. , Jia , Z. J. , Kraehmer , R. and Fraser‐Reid , B. 1999 . Concerning the reactivities of the C‐1, C‐2 and C‐6 hydroxy groups of myo‐inositol . J.Chem.Soc.Perkin , 1 : 3591 – 3596 .
   Google Scholar
• Anilkumar , G. , Nair , L. G. and Fraser‐Reid , B. 2000 . Targeted glycosyl donor delivery for siteselectivity glycosylation . Org. Letters , 2 : 2587 – 2589 .
   PubMed Web of Science ®Google Scholar
• Anilkumar , G. , Gilbert , M. R. and Fraser‐Reid , B. 2000 . Regioselective mannosylation routes to the antigenic myo-inositol component of Mycobacterium tuberculosis B . Tetrahedron , 56 : 1993 – 1997 .
   Web of Science ®Google Scholar
• Fraser‐Reid , B. , Anilkumar , G. N. , Nair , L. G. , Radhakrishnan , K. V. , López , J. C. , Gómez , A. M. and Uriel , C. 2002 . Evidence for efficient unpromoted regioselective reactions of vicinal and nonvicinal diols . Aust. J. Chem. , 55 : 123 – 130 .
   Web of Science ®Google Scholar
• Fraser‐Reid , B. , López , J. C. , Radhakrishnan , K. V. , Nandakumar , M. V. , Gómez , A. M. and Uriel , C. 2002 . One pot/two donors/one diol give one differentiated trisaccharide: powerful evidence for reciprocal donor acceptor selectivity (RDAS) . Chem. Commun. , : 2104 – 2105 .
   PubMed Web of Science ®Google Scholar
• Uriel , C. , Gómez , A. , López , J. C. and Fraser‐Reid , B. 2003 . Further insight into “matching” of donors and acceptors via reciprocal donor acceptor selectivity (RDAS) studies . Synlett , : 2203 – 2207 .
   Web of Science ®Google Scholar
• López , J. C. , Gómez , A. M. , Uriel , C. and Fraser‐Reid , B. 2003 . Thioglycoside and trichloroacetimidate donors in regioselective glycosidations Comparison with n‐pentenyl glycosides . Tetrahedron Lett. , 44 : 1417 – 1420 .
   Web of Science ®Google Scholar
• Fraser‐Reid , B. , López , J. C. , Radhakrishnan , K. V. , Mach , M. , Schlueter , U. , Gómez , A. M. and Uriel , C. 2002 . Unexpected role of O‐2 “protecting” groups of glycosyl donors in mediating regioselective glycosidation . J. Am. Chem. Soc. , 124 : 3198
   PubMed Web of Science ®Google Scholar
• Fraser‐Reid , B. , López , J. C. , Radhakrishnan , K. V. , Mach , M. , Schlueter , U. , Gómez , A. M. and Uriel , C. 2002 . reciprocal donor acceptor selectivity (RDAS): a new concept for “matching” donors with acceptors . Can. J. Chem. , 80 : 1075 – 1087 .
   Web of Science ®Google Scholar
• Mootoo , D. R. , Konradsson , P. , Udodong , U. and Fraser‐Reid , B. 1988 . Armed and disarmed n-pentenyl glycosides in saccharide couplings leading to oligosaccharides . J. Am. Chem. Soc. , 110 : 5583 – 5584 .
   Web of Science ®Google Scholar
• Fraser‐Reid , B. , Wu , Z. , Udodong , U. E. and Ottosson , H. 1990 . Armed/disarmed effects in glycosyl donors: rationalization and sidetracking . J. Org. Chem. , 55 : 6068 – 6070 .
   Web of Science ®Google Scholar
• Fraser‐Reid , B. , Grimme , S. , Piacenza , P. , Mach , M. and Schlueter , U. 2003 . Orthoesters versus 2‐O‐acyl glycosides as glycosyl donors: theorectical and experimental studies . Chem. Eur. J. , 9 : 4687 – 4692 .
   PubMed Web of Science ®Google Scholar
• Nicolaou , K. C. , Winssinger , N. , Pastor , J. and DeRoose , F. A. 1997 . General and highly efficient solid phase synthesis of oligosaccharides. Total synthesis of a heptasaccharide phytoalexin elicitor (HPE) . J. Am. Chem. Soc. , 119 : 449 – 450 .
   Web of Science ®Google Scholar
• Mayer , T. G. and Schmidt , R. R. 1999 . Glycosyl phosphatidylinositol (GPI) anchor synthesis based on versatile building blocks—Total synthesis of a GPI anchor of yeast . Eur. J. Org. Chem. , : 1153 – 1165 .
   Web of Science ®Google Scholar