Reactions of Nucleophiles with Reactive Intermediates in the 3,4,6‐Tri‐O‐benzyl‐d‐glucal–TfOH–n‐Bu₄NI Reaction System

References

• Sawamoto , M. , Okamoto , C. and Higashimura , T. 1987 . Hydrogen iodide/zinc iodide: a new initiating system for living cationic polymerization of vinyl ethers at room temperature . Macromolecules , 20 ( 11 ) : 2693 – 2697 .
   Google Scholar
• Miyamoto , M. , Sawamoto , M. and Higashimura , T. 1984 . Living polymerization of isobutyl vinyl ether with hydrogen iodide/iodine initiating system . Macromolecules , 17 ( 3 ) : 265 – 268 .
   Google Scholar
• Kojima , K. , Sawamoto , M. and Higashimura , T. 1989 . Living cationic polymerization by electrophile Lewis acid initiating systems. 3. Living cationic polyerization of isobutyl vinyl ether by hydrogen iodide Lewis acid initiating systems—effects of Lewis acid activators and polymerization kinetics . Macromolecules , 22 ( 4 ) : 1552 – 1557 .
   Google Scholar
• Hall , R. H. , Jordaan , A. and Lourens , G. J. 1973 . Reaction of chlorosulfonyl isocyanate with unsaturated sugars . J. Chem. Soc., Perkin Trans. 1 , : 38 – 44 .
   Google Scholar
• Kamigaito , M. , Sawamoto , M. and Higashimura , T. 1991 . Living cationic polymerization of isobutyl vinyl ether by RCOOH/Lewis acid initiating systems: effects of carboxylate ions and Lewis acid activators . Macromolecules , 24 ( 14 ) : 3988 – 3992 .
   Google Scholar
• Aoshima , S. and Higashimura , T. 1989 . Living cationic polymerization of vinyl monomers by organo‐aluminum halides. 3. Living polymerization of isobutyl vinyl ether by EtAlCl2 in the presence of ester additives . Macromolecules , 22 ( 3 ) : 1009 – 1013 .
   Google Scholar
• Kamigaito , M. , Sawamoto , M. and Higashimura , T. 1992 . Living cationic polymerization of isobutyl vinyl ether by benzoic‐acid derivatives zinc‐chloride initiating systems—slow interconversion between dormant and activated growing species . Macromolecules , 25 ( 24 ) : 6400 – 6406 .
   Google Scholar
• Hashimoto , T. , Takahashi , T. and Kodaira , T. 2000 . Living cationic polymerization of vinyl ethers with carboxylic acid/tin tetrahalide initiating systems. III. Benzoic acid and related weakly acidic carboxylic acids for the living polymerization of isobutyl vinyl ether . J. Polym. Sci., A: Polym. Chem. , 38 ( 4 ) : 781 – 784 .
   Google Scholar
• Cho , C. G. , Feit , B. A. , Webster , O. W. , du Pont de Nemours , E. I. and and Co. Living Cationic Polymerization of Alkyl Vinyl Ethers . U.S. Patent 5, 196, 491 . March 23, 1993 .
   Google Scholar
• Cho , C. G. , Feit , B. A. and Webster , O. W. 1990 . Cationic polymerization of isobutyl vinyl ether—livingness enhancement by dialkyl sulfides . Macromolecles , 23 ( 7 ) : 1918 – 1923 .
   Google Scholar
• Cho , C. G. , Feit , B. A. and Webster , O. W. 1992 . Initiation of vinyl ether polymerization by trimethylsilyl triflate, dimethyl sulfide, and adventitious water . Macromolecules , 25 ( 8 ) : 2081 – 2085 .
   Google Scholar
• Faust , R. and Kennedy , J. P. 1987 . Living carbocationic polymerization. IV. Living polymerization of isobutylene . J. Polym. Sci., Polym. Chem. Ed. , 25 ( 7 ) : 1847 – 1869 .
   Google Scholar
• Faust , R. and Kennedy , J. P. 1986 . Living carbocationic polymerization. III. Demonstration of the living polymerization of isobutylene . Polym. Bull. , 15 ( 4 ) : 317 – 323 .
   Google Scholar
• Matyjaszewski , K. 1988 . Activated esters in the cationic polymerization of styrenes . Makromol. Chem., Macromol. Symp. , 13–14 : 433 – 441 .
   Google Scholar
• Kasuto , Kelson I. 2001 . Ph.D. thesis Tel‐Aviv University .
   Google Scholar
• Nuyken , O. , Kroner , H. and Aechtner , S. 1990 . Living cationic polymerization of vinyl ethers . Makromol. Chem., Macromol. Symp. , 32 : 181 – 197 .
   Google Scholar
• Goethals , E. J. , Haucourt , N. and Peng , L. B. 1994 . Some new developments in vinyl ether polymerization . Macromol. Symp. , 85 : 97 – 113 .
   Google Scholar
• Suzuki , K. , Sulikowski , G. A. , Friesen , R. W. and Danishefsky , S. J. 1990 . Application of substituent‐controlled oxidative coupling of glycals in a synthesis and structural corroboration of Ciclamycin‐0—new possibilities for the construction of hybrid anthracyclines . J. Am. Chem. Soc. , 112 ( 24 ) : 8895 – 8902 .
   Google Scholar
• Raghavan , S. and Kahne , D. 1993 . A one‐step synthesis of the Ciclamycin trisaccharide . J. Am. Chem. Soc. , 115 ( 4 ) : 1580 – 1581 .
   Google Scholar
• Thiem , J. and Klaffke , W. 1989 . Facile stereospecific synthesis of deoxyfucosyl disaccharide units of anthracyclines . J. Org. Chem. , 54 ( 8 ) : 2006 – 2009 .
   Google Scholar
• Czernecki , S. , Leteux , C. and Veyrières , A. 1992 . Versatile behavior of O‐stannylated d‐glucal towards halogens . Tetrahedron Lett. , 33 ( 2 ) : 221 – 224 .
   Google Scholar
• Mootoo , D. R. , Kondradsson , 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 ( 16 ) : 5583 – 5584 .
   Google Scholar
• Roy , R. , Anderson , F. O. and Letellier , M. 1992 . Active and latent thioglycosyl donors in oligosaccharide synthesis—application to the synthesis of α‐sialosides . Tetrahedron Lett. , 33 ( 41 ) : 6053 – 6056 .
   Google Scholar
• Sliedregt , L. A.J.M. , Zegelaar‐Jaarverld , K. , van der Marel , G. A. and van Boom , J. H. 1993 . Use of 4‐nitrophenylthio‐β‐d‐glycosides in oligosaccharide synthesis—a critical—evaluation . Synlett , : 337 – 355 .
   Google Scholar
• Belluci , G. , Chiappe , C. , D'Andrea , F. and Lo Morro , G. 1997 . Stereoelectronic control in two‐step additions to tri‐O‐benzyl‐d‐glucal initiated by electrophilic halogens . Tetrahedron , 53 ( 9 ) : 3417 – 3424 .
   Google Scholar
• Friesen , R. W. and Danishefsky , S. J. 1990 . On the use of the haloetherification method to synthesize fully functionalized disaccharides . Tetrahedron , 46 ( 1 ) : 103 – 112 .
   Google Scholar
• Thiem , J. and Meyer , B. 1980 . Syntheses with iodo‐ and bromotrimethylsilane in saccharide chemistry . Chem. Ber. , 113 ( 9 ) : 3075 – 3085 .
   Google Scholar
• Miljković , D. , Djurendić , E. , Vukojevic , N. , Gaši , K. and Csanádi , J. 1992 . A novel route to 2‐deoxy‐2‐iodo‐d‐mannopyranose derivatives . J. Carbohydr. Res. , 233 : 251 – 253 .
   Google Scholar
• Dyong , I. , Meyer , W. and Thiem , J. 1986 . Syntheses of biologically important carbohydrates. 35. Synthesis of exocyclic saccharide enol ethers and their conversion into branched‐chain carbohydrates . Liebigs Ann. Chem. , : 613 – 624 .
   Google Scholar
• Nadkarni , S. and Williams , N. R. 1965 . Displacement reactions of galactose 6‐sulfonate derivatives . J. Chem. Soc. , : 3496 – 3498 .
   Google Scholar
• Frische , K. and Schmidt , R. R. 1994 . Glycal‐1‐ylmethylphosphonates—precursors of glycosyltransferase inhibitors . Liebigs Ann. Chem. , : 297 – 303 .
   Google Scholar
• Bolitt , V. , Mioskowski , C. , Lee , S.‐G. and Falck , J. R. 1990 . Direct preparation of 2‐deoxy‐d‐glucopyranosides from glucals without Ferrier rearrangement . J. Org. Chem. , 55 ( 23 ) : 5812 – 5813 .
   Web of Science ®Google Scholar
• France , C. J. , McFarlane , I. M. , Newton , C. G. , Pitchen , P. and Webster , M. 1993 . Straightforward homochiral synthesis of the lactone moiety of mevinic acids . Tetrahedron Lett. , 34 ( 10 ) : 1635 – 1638 .
   Google Scholar
• Sabesan , S. and Neira , S. 1991 . Synthesis of 2‐deoxy sugars from glycals . J. Org. Chem. , 56 ( 18 ) : 5468 – 5472 .
   Web of Science ®Google Scholar
• Toshima , K. , Nagai , H. , Ushiki , Y. and Matsumura , S. 1998 . Novel glycosidations of glycals using BCl3 or BBr3 as a promoter for catalytic and stereoselective syntheses of 2‐deoxy‐α‐glycosides . Synlett , : 1007 – 1009 .
   Google Scholar
• Wakamatsu , T. , Nakamura , H. and Naka , E. 1986 . Synthetic studies on antibiotic macrodiolide. Synthesis of the A‐segment of Elaiophylin . Tetrahedron Lett. , 27 ( 33 ) : 3895 – 3898 .
   Google Scholar
• Toshima , K. , Tatsuta , K. and Kinoshita , M. 1988 . Total synthesis of Elaiophylin (Azalomycin‐β) . Bull. Chem. Soc. Jpn. , 61 ( 7 ) : 2369 – 2381 .
   Google Scholar
• Pachamuthu , K. and Vankar , Y. D. 2001 . Ceric ammonium nitrate‐catalyzed tetrahydropyranylation of alcohols and synthesis of 2‐deoxy‐O‐glycosides . J. Org. Chem. , 66 ( 22 ) : 7511 – 7513 .
   PubMed Web of Science ®Google Scholar
• Ferrier , R. J. and Collins , P. M. 1972 . Monosaccharide Chemistry 173 – 178 . Harmondsworth : Penguin Library of Physical Sciences: Chemistry .
   Google Scholar
• Zein , N. , Sinha , A. M. , McGahren , W. J. and Ellestad , G. A. 1988 . Calicheamicin‐γ‐1‐I—an antitumor antibiotic that cleaves double‐stranded DNA site specifically . Science , 240 ( 4856 ) : 1198 – 1201 .
   PubMed Web of Science ®Google Scholar
• Thiem , J. and Meyer , B. 1981 . Studies on the structure of Olivomycin A and Mithramycin by proton and carbon‐13 nuclear magnetic resonance spectroscopy . Tetrahedron , 37 ( 3 ) : 551 – 558 .
   Google Scholar
• Roush , W. , Hartz , R. A. and Gustin , D. J. 1999 . Total synthesis of Olivomycin A . J. Am. Chem. Soc. , 121 ( 9 ) : 1990 – 1991 .
   Google Scholar
• Schene , H. and Waldmann , H. 1999 . Synthesis of deoxy glycosides under neutral conditions in LiClO4/solvent mixtures . Synthesis , : 1411 – 1422 .
   Web of Science ®Google Scholar
• Garner , P. and Anderson , J. T. 1997 . A rationally designed chiral auxiliary for hydroxyalkyl radicals leads to exceptional ρ‐stereocontrol . Tetrahedron Lett. , 38 ( 38 ) : 6647 – 6650 .
   Google Scholar
• Nicolaou , K. C. , Pastor , J. , Barluenga , S. and Winssinger , N. 1998 . Polymer‐supported selenium reagents for organic synthesis . Chem. Commun. , : 1947 – 1948 .
   Web of Science ®Google Scholar
• Hashimoto , S. , Yanagiya , Y. , Honda , T. and Ikegami , S. 1992 . A stereocontrolled construction of 2‐deoxy‐β‐glycosidic linkages via 1,2‐trans‐β‐glycosidation of 2‐deoxy‐2‐[p‐methoxyphenyl)thio]glycopyranosyl N,N,N′,N′‐tetramethylphosphoroamidates . Chem. Lett. , : 1511 – 1514 .
   Google Scholar
• Hashimoto , S. , Sano , A. , Sakamoto , H. , Nakajima , M. , Yanagiya , Y. and Ikegami , S. 1995 . An attempt at the direct construction of 2‐deoxy‐β‐glycosidic linkages capitalizing on 2‐deoxyglycopyranosyl diethyl phosphites as glycosyl donors . Synlett , : 1271 – 1273 .
   Web of Science ®Google Scholar
• Dios , A. , Nativi , C. , Capozzi , G. and Franck , R. W. 1999 . Novel stereoelectronic behavior of bicyclic glycosyl donors: application to the synthesis of both 2‐deoxy‐α‐ and ‐β‐glycosides . Eur. J. Org. Chem. , : 1869 – 1874 .
   Google Scholar
• Descotes , G. and Martin , J.‐C. 1977 . Isomerization of 1,5‐anhydro‐3,4,6‐tri‐O‐benzyl‐1,2‐dideoxy‐d‐arabino‐hex‐1‐enitol in the presence of Lewis acids . Carbohydr. Res. , 56 ( 1 ) : 168 – 172 .
   Google Scholar