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Original Articles

Improved Synthesis of 1‐Benzenesulfinyl Piperidine and Analogs for the Activation of Thioglycosides in Conjunction with Trifluoromethanesulfonic AnhydrideFootnote*

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Pages 415-424 | Accepted 21 Feb 2005, Published online: 16 Aug 2006

References

  • Crich , D. and Smith , M. 2001 . 1‐Benzenesulfinyl piperidine (BSP)/trifluoromethanesulfonic anhydride: a potent combination of shelf‐stable reagents for the low temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages . J. Am. Chem. Soc. , 123 : 9015 – 9020 .
  • Crich , D. and Lim , L. B.L. 2004 . Glycosylation with sulfoxides and sulfinates as donors or promoters . Org. React. , 64 : 115 – 251 .
  • Crich , D. and Li , H. 2002 . Synthesis of the Salmonella Type E1 core trisaccharide as a probe for the generality of 1‐benzenesulfinyl piperidine/triflic anhydride combination for glycosidic bond formation . J. Org. Chem. , 67 : 4640 – 4646 .
  • Crich , D. , de la Mora , M. A. and Cruz , R. 2002 . Synthesis of the mannosyl erythritol lipid MEL A; confirmation of the configuration of the “meso‐erythritol” moiety . Tetrahedron , 58 : 35 – 44 .
  • Dudkin , V. Y. and Crich , D. 2003 . A short synthesis of the trisaccharide building block of the N‐linked glycans . Tetrahedron Lett. , 44 : 1787 – 1789 .
  • Crich , D. and Yao , Q. 2004 . The benzylidene acetal fragmentation route to 6‐deoxy sugars: direct reductive cleavage in the presence of ether protecting groups permitting the efficient, highly stereocontrolled synthesis of β‐D‐rhamnosides from d‐mannosyl glycosyl donors. Total synthesis of α‐D‐Gal‐(1→3)‐α‐D‐Rha‐(1→3)-β-D-Rha)‐(1→4)-β‐D‐Glu‐OMe, the repeating unit of the antigenic lipopolysaccharide from Escherichia hermannii ATCC 33650 and 33652 . J. Am. Chem. Soc. , 126 : 8232 – 8236 .
  • Crich , D. , Banerjee , A. and Yao , Q. 2004 . Direct chemical synthesis of the β‐D‐mannans: the β‐(1→2)‐ and β‐(1→4)‐series . J. Am. Chem. Soc. , 126 : 14930 – 14934 .
  • Mong , T. K.‐K. , Lee , H.‐K. , Duron , S. G. and Wong , C.‐H. 2003 . Reactivity‐based one‐pot total synthesis of fucose GM1 oligosaccharide: a sialylated antigenic epitope of small‐cell ling cancer . Proc. Natl. Acad. Sci. USA , 100 : 797 – 802 .
  • Wang , Y. , Huang , X. , Zhang , L.‐H. and Ye , X.‐S. 2004 . A four component one‐pot synthesis of α‐Gal pentasaccharide . Org. Lett. , 6 : 4415 – 4417 .
  • Codée , J. D.C. , van den Bos , L. J. , Litjens , R. E.J.N. , Overkleeft , H. S. , van Boeckel , C. A.A. , van Boom , J. H. and van der Marel , G. A. 2004 . Chemoselective glycosylations using sulfonium triflate activator systems . Tetrahedron , 60 : 1057 – 1064 .
  • Gadikota , R. R. , Callam , C. S. , Wagner , T. , Del Fraino , B. and Lowary , T. L. 2003 . 2,3‐Anhydro sugars in glycoside bond synthesis. Highly stereoselective syntheses of oligosaccharides containing α‐ and β‐arabinofuranosyl linkages . J. Am. Chem. Soc. , 125 : 4155 – 4165 .
  • Yamago , S. , Yamada , H. , Maruyama , T. and Yoshida , J.‐I. 2004 . Iterative glycosylation of 2‐deoxy‐2‐aminothioglycosides and its application to the combinatorial synthesis of linear oligoglucosamines . Angew. Chem. Int. Ed. Engl. , 43 : 2145 – 2148 .
  • van den Bos , L. , Codée , J. D.C. , van der Toorn , J. C. , Boltje , T. J. , van Boom , J. H. , Overkleeft , H. S. and van der Marel , G. A. 2004 . Thioglycuronides: synthesis and application in the assembly of acidic oligosaccharides . Org. Lett. , 6 : 2165 – 2168 .
  • Douglass , I. B. and Norton , R. V. 1968 . Superior method for preparing sulfinyl chlorides . J. Org. Chem. , 33 : 2104 – 2106 .
  • Craig , D. , Daniels , K. and MacKenzie , A. R. 1993 . Additive Pummerer reactions of vinylic sulfoxides. Synthesis of γ‐hydroxy‐α,β‐unsaturated esters, α‐hydroxyketones, and 2‐phenylsulfenyl aldehydes and primary alcohols . Tetrahedron , 49 : 11263 – 11304 .
  • Kurzer , F. 1963 . p‐Toluenesulfinyl chloride . Org. Synth. Coll. Vol. , 4 : 937 – 939 . For an earlier version of this protocol see:
  • Bujnicki , B. , Drabowicz , J. , Mikolajczyk , M. , Kolbe , A. and Stefaniak , L. 1996 . Protonation of sulfinamides. Does it occur at oxygen or nitrogen? . J. Org. Chem. , 61 : 7593 – 7596 .
  • Matsuo , J.‐I. , Iida , D. , Tatani , K. and Mukaiyama , T. 2002 . A new method for oxidation of various alcohols to the corresponding carbonyl compounds by using N‐t‐butylbenzenesulfinimidoyl chloride . Bull. Chem. Soc. Jpn. , 75 : 223 – 234 .
  • Crich , D. and Sun , S. 1998 . Direct chemical synthesis of β‐mannopyranosides and other glycosides via glycosyl triflates . Tetrahedron , 54 : 8321 – 8348 .
  • Crich , D. , Smith , M. , Yao , Q. and Picione , J. 2001 . 2,4,6‐Tri‐tert‐butylpyrimidine (TTBP): A cost effective, readily available alternative to the hindered base 2,6‐di‐tert‐butylpyridine and its 4‐substituted derivatives in glycosylation and other reactions . Synthesis , : 323 – 326 .
  • Gin , D. Y. 2001 . “ Dehydrative glycosylation with 1‐hydroxy donors ” . In Glycochemistry. Principles, Synthesis, and Applications Edited by: Wang , P. and Bertozzi , C. R. 33 – 52 . New York : Dekker .
  • Codée , J. D.C. , Litjens , R. E.J.N. , den Heeten , R. , Overkleeft , H. S. , van Boom , J. H. and van der Marel , G. A. 2003 . Ph2SO/Tf2O: a powerful promoter system in chemoselective glycosylations using thioglycosides . Org. Lett. , 5 : 1519 – 1522 .
  • Codée , J. D.C. , van den Bos , J. , Litjens , R. E.J.N. , Overkleeft , H. S. , van Boom , J. H. and van der Marel , G. A. 2003 . Sequential one‐pot glycosylations using 1‐hydroxy and 1‐thiodonors . Org. Lett. , 5 : 1947 – 1950 .
  • Crich , D. and Vinod , A. U. 2005 . 6‐O‐Benzyl and 6‐O‐silyl‐N‐acetyl‐2‐amino‐2N,3‐O‐carbonyl‐2‐deoxyglucosides: Effective glycosyl acceptors in the glucosamine 4‐OH series. Effect of anomeric stereochemistry on the removal of the oxazolidinone group . J. Org. Chem. , 70 : 1291 – 1296 .
  • Crich , D. , de la Mora , M. and Vinod , A. U. 2003 . Influence of the 4,6‐O‐benzylidene, 4,6‐O‐phenylboronate, and 4,6‐O‐polystyrylboronate protecting groups on the stereochemical outcome of thioglycoside‐based glycosylations mediated by 1‐benzenesulfinyl piperidine/triflic anhydride and N‐iodosuccinimide . J. Org. Chem. , : 8142 – 8148 .
  • Crich , D. , Hutton , T. K. , Banerjee , A. , Jayalath , P. and Picione , J. 2005 . Disarming, non‐participating 2‐O‐protecting groups in manno‐ and rhamnopyranosylation: scope and limitations of sulfonates, vinylogous esters, phosphates, cyanates, and nitrates . Tetrahedron: Asymmetry , 16 : 105 – 119 .
  • The differing polarity of the byproducts from the sulfinamide method and the diphenyl sulfoxide methods is an advantage, and it is sometimes found that switching from one of these activating systems to the other can greatly facilitate purification.
  • Durón , S. G. , Polat , T. and Wong , C.‐H. 2004 . N‐(Phenylthio)‐ϵ‐caprolactam: a new promoter for the activation of thioglycosides . Org. Lett. , 6 : 839 – 841 .
  • Norberg , T. 1996 . “ Glycosylation properties and reactivity of thioglycosides, sulfoxides and other S‐glycosides ” . In Modern Methods in Carbohydrate Synthesis Edited by: Khan , S. H. and O'Neill , R. A. 82 – 106 . Amsterdam : Harwood Academic Publishers .
  • Garegg , P. J. 1997 . Thioglycosides as glycosyl donors in oligosaccharide synthesis . Adv. Carbohydr. Chem. Biochem. , 52 : 179 – 266 .
  • Oscarson , S. 2000 . “ Thioglycosides ” . In Carbohydrates in Chemistry and Biology Edited by: Ernst , B. , Hart , G. W. and Sinaÿ , P. Vol. 1 , 93 – 116 . Weinheim : Wiley‐VCH .
  • Maricich , T. J. and Angeletakis , C. N. 1984 . Reaction of benzenesulfinyl azide with thiols and amines. Preparation of thiosulfinates and sulfinamides . J. Org. Chem. , 49 : 1931 – 1934 .
  • Garegg , P. and Norberg , T. 1979 . Observations on silver trifluoromethanesulfonate‐promoted synthesis of 1,2‐trans glycosides for acylated glycosyl bromides . Acta Chem. Scand. , 33 : 116 – 118 .
  • An erroneous data set was inadvertantly recorded previously1 for this compound. The correct data are given here.

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