Skip to main content
SpringerLink
Log in

“Active–Latent” Thioglycosyl Donors and Acceptors in Oligosaccharide Syntheses

  • Chapter
  • First Online:
Reactivity Tuning in Oligosaccharide Assembly

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 301))

Abstract

The fine tuning of thioglycosides used as glycosyl donors occurs through careful manipulations of the aglycon’s nucleofugality, for example, by using “active–latent” principles. In the first section, the control of the relative leaving group abilities will be discussed in terms of electronic factors, including electron-donating/withdrawing substituents. In the second section, the nucleofugality will be adjusted by steric factors. Quantitative reactivity relationships will then be documented followed by presentation of other controlling elements including locked conformations, solvents, and promoters that will be illustrated throughout.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Paulsen H (1982) Angew Chem Int Ed Engl 21:155

    Article  Google Scholar 

  2. Schmidt RR (1986) Angew Chem Int Ed Engl 25:212

    Article  Google Scholar 

  3. Banoub J, Boullanger P, Lafont D (1992) Chem Rev 92:1167

    Article  CAS  Google Scholar 

  4. Toshima K, Tatsuta K (1993) Chem Rev 93:1503

    Article  CAS  Google Scholar 

  5. Schmidt RR, Kinzy W (1994) Adv Carbohydr Chem Biochem 50:1419

    Google Scholar 

  6. Danishefsky SJ, Bilodeau MT (1996) Angew Chem Int Ed Engl 35:1380

    Article  CAS  Google Scholar 

  7. Boons GJ (1996) Tetrehedron 52:1095

    Article  CAS  Google Scholar 

  8. Norberg T (1996) In: Khan SH, O’Neill RA (eds) Modern methods in carbohydrate synthesis. Harwood Academic, Amsterdam, p 82

    Google Scholar 

  9. Garegg PJ (1997) Adv Carbohydr Chem Biochem 52:179

    Article  CAS  Google Scholar 

  10. Fraser-Reid B, Madsen R (1997) In: Hanessian S (ed) Preparative carbohydrate chemistry. Marcel Dekker, New York, pp 339–356

    Google Scholar 

  11. Davis B (2000) J Chem Soc Perkin Trans 1 2137

    Google Scholar 

  12. Boons GJ, Demchenko AV (2000) Chem Rev 100:4539

    Article  CAS  Google Scholar 

  13. Hanessian S, Lou B (2000) Chem Rev 100:4443

    Article  CAS  Google Scholar 

  14. Seeberger PH, Haase WC (2000) Chem Rev 100:4349

    Article  CAS  Google Scholar 

  15. Koeller KM, Wong CH (2000) Chem Rev 100:4465

    Article  CAS  Google Scholar 

  16. Oscarson S (2000) In: Ernst B, Hart GW, Sinay P (eds) Carbohydrates in chemistry and biology, vol 1. Wiley, Weinheim, pp 93–116

    Google Scholar 

  17. Nicolaou KC, Mitchell HJ (2001) Angew Chem Int Ed Engl 40:1576

    Article  CAS  Google Scholar 

  18. Demchenko AV (2003) Curr Org Chem 7:35

    Article  CAS  Google Scholar 

  19. El Ashry ESH, Awad LF, Atta AI (2006) Tetrahedron 62:2943

    Google Scholar 

  20. Crich D (2007) ACS Symp Ser 960:60

    Article  CAS  Google Scholar 

  21. Cai F, Wu B, Crich D (2009) Adv Carbohydr Chem Biochem 62:251

    Article  CAS  Google Scholar 

  22. Roy R, Andersson FO, Letellier M (1992) Tetrahedron Lett 33:6053

    Article  CAS  Google Scholar 

  23. Cao S, Meunier SJ, Andersson FO, Letellier M, Roy R (1994) Tetrahedron Asymmetry 5:2303

    Article  CAS  Google Scholar 

  24. Cao S, Roy R (1996) Tetrahedron Lett 37:3421

    Article  CAS  Google Scholar 

  25. Cao S, Hernández-Matéo F, Roy R (1998) J Carbohydr Chem 17:609

    Article  CAS  Google Scholar 

  26. Sasaki M, Tachibana K, Nakanishi J (1991) Tetrahedron Lett 32:6873

    Article  CAS  Google Scholar 

  27. Veeneman GH, van Boom JH (1990) Tetrahedron Lett 31:275

    Article  CAS  Google Scholar 

  28. Veeneman GH, van Leeuwen SH, van Boom JH (1990) Tetrahedron Lett 31:1131

    Google Scholar 

  29. Konradsson P, Udolong UE, Fraser-Reid B (1990) Tetrahedron Lett 31:4313

    Article  CAS  Google Scholar 

  30. Roy R, Tropper FD, Cao S, Kim JM (1997) ACS Symp Ser 659:163

    Article  CAS  Google Scholar 

  31. Roy R (1997) In: Sasson Y, Neumann R (eds) Handbook of phase transfer catalysis, chap 7. Chapman and Hall, London, pp 244–275

    Google Scholar 

  32. Roy R, Letellier M, Fenske E, Jarell HC (1990) J Chem Soc Chem Commun 378

    Google Scholar 

  33. Kuhn R, Lutz P, McDonald DL (1966) Chem Ber 99:611

    Article  CAS  Google Scholar 

  34. Roy R, Laferrière CA (1990) Can J Chem 68:2045

    Article  CAS  Google Scholar 

  35. Murase T, Ishida H, Kiso M, Hasegawa A (1988) Carbohydr Res 184:C1

    Article  CAS  Google Scholar 

  36. Fügedi P, Garegg PJ (1986) Carbohydr Res 149:C9

    Article  Google Scholar 

  37. Ogawa T, Sugimoto M (1984) Carbohydr Res 128:Cl

    Google Scholar 

  38. Hasegawa A, Nagahama T, Ohki H, Hotta K, Ishida H, Kiso J (1991) J Carbohydr Chem 10:493

    Article  CAS  Google Scholar 

  39. Kirchner E, Thiem F, Dernick R, Henkeshoren J, Thiem J (1988) J Carbohydr Chem 7:453

    Article  CAS  Google Scholar 

  40. Paulsen H, Tietz H (1984) Carbohydr Res 125:47

    Article  CAS  Google Scholar 

  41. Okamato K, Goto T (1990) Tetrahedron 46:5835

    Article  Google Scholar 

  42. Lönn H, Stenvall K (1992) Tetrahedron Lett 33:115

    Google Scholar 

  43. Varki A (1993) Glycobiology 3:97

    Article  CAS  Google Scholar 

  44. Chen X, Varki A (2010) ACS Chem Biol 5:163

    Article  CAS  Google Scholar 

  45. Angata T, Varki A (2002) Chem Rev 102:439

    Article  CAS  Google Scholar 

  46. Hanai N, Nores GA, MacLeod C, Torres-Mendez CR, Hakomori SJ (1988) Biol Chem 263:10915

    CAS  Google Scholar 

  47. Roy R (2002) J Carbohydr Chem 21:769

    Article  CAS  Google Scholar 

  48. Sliedregt LAJM, Zegelaar-Jaarsveld K, van der Marel GA, van Boom JH (1993) Synlett 5:335

    Article  Google Scholar 

  49. Sliedregt LAJM, van der Marel GA, van Boom JH (1994) Proc Indian Acad Sci 106:1213

    CAS  Google Scholar 

  50. Andersson F, Birberg W, Fugedi P, Garegg PJ, Nashed M, Pilotti A (1989) ACS Symp Ser 386:117

    Article  CAS  Google Scholar 

  51. Ohrui H, Nishida Y, Itoh H, Meguro H (1991) J Org Chem 56:1726

    Article  CAS  Google Scholar 

  52. Bongat AFG, Demchenko AV (2007) Carbohydr Res 342:374

    Article  CAS  Google Scholar 

  53. Cao S (1996) Ph.D. Dissertation, University of Ottawa, Canada

    Google Scholar 

  54. Gan Z, Cao S, Wu Q, Roy R (1999) J Carbohydr Chem 18:755

    Article  CAS  Google Scholar 

  55. Garegg PJ, Hultberg H, Wallin S (1982) Carbohydr Res 108:97

    Article  CAS  Google Scholar 

  56. Kahne D, Walker S, Cheng Y, Engen D (1989) J Am Chem Soc 111:6881

    Article  CAS  Google Scholar 

  57. Raghavan S, Kahne D (1993) J Am Chem Soc 115:1580

    Article  CAS  Google Scholar 

  58. Blanc-Muesser M, Defaye J, Driguez H (1978) Carbohydr Res 67:305

    Article  CAS  Google Scholar 

  59. Boons G-J, Geurtsen R, Holmes D (1995) Tetrahedron Lett 36:6325

    Article  CAS  Google Scholar 

  60. Geurtsen R, Holmes DS, Boons G-J (1997) J Org Chem 62:8145

    Article  CAS  Google Scholar 

  61. Geurtsen R, Boons G-J (2002) Tetrahedron Lett 43:9429

    Article  CAS  Google Scholar 

  62. Boons GJ, Isles S (1994) Tetrahedron Lett 35:3593

    Article  CAS  Google Scholar 

  63. Boons GJ, Isles S (1996) J Org Chem 61:4262

    Article  CAS  Google Scholar 

  64. Boons GJ, Heskamp B, Hout F (1996) Angew Chem Int Ed Engl 35:2845

    Article  CAS  Google Scholar 

  65. Crich D, Wu B (2008) Org Lett 10:4033

    Article  CAS  Google Scholar 

  66. Strijtveen B, Kellog RM (1986) J Org Chem 51:3664

    Article  CAS  Google Scholar 

  67. Lemieux RU, Hendriks KB, Stick RV, James K (1975) J Am Chem Soc 97:4056

    Article  CAS  Google Scholar 

  68. Crich D, Li W (2007) J Org Chem 72:2387

    Article  CAS  Google Scholar 

  69. Crich D, Li W (2007) J Org Chem 72:7794

    Article  CAS  Google Scholar 

  70. Tanaka H, Nishiura Y, Takahashi T (2006) J Am Chem Soc 128:7124

    Article  CAS  Google Scholar 

  71. Farris MD, DeMeo C (2007) Tetrahedron Lett 48:1225

    Article  CAS  Google Scholar 

  72. Grattan TJ, Whitehurst JS (1990) J Chem Soc Perkin Trans 1 11

    Google Scholar 

  73. Lahmann M, Oscarson S (2002) Can J Chem 80:889

    Article  CAS  Google Scholar 

  74. Zhang Z, Ollmann IR, Ye XS, Wischnat R, Baasov T, Wong CH (1999) J Am Chem Soc 121:745

    Google Scholar 

  75. Douglas NL, Ley SV, Lucking U, Warriner SL (1998) J Chem Soc Perkin Trans 1 51

    Google Scholar 

  76. Wu C-Y, Wong C-H (2011) Programmable one-pot glycosylation. In: Topics in current chemistry. Springer, Heidelberg. doi: 10.1007/128_2010_109

    Google Scholar 

  77. Son SH, Tano C, Furuike T, Sakairi N (2009) Carbohydr Res 344:285

    Article  CAS  Google Scholar 

  78. Pastuch G, Wandzik I, Szeja W (200) Tetrahedron Lett 41:9923

    Google Scholar 

  79. Davis BG, Ward SJ, Rendle PM (2001) Chem Commun 189

    Google Scholar 

  80. Ley SV, Priepke HWM (1994) Angew Chem Int Ed Engl 33:2292

    Google Scholar 

  81. Boons G-J, Grice P, Leslie R, Ley SV, Yeung LL (1993) Tetrahedron Lett 34:8523

    Article  CAS  Google Scholar 

  82. Gómez AM (2011) A survey of Ley’s reactivity tuning in oligosaccharide synthesis. In: Topics in current chemistry. Springer, Heidelberg. doi: 10.1007/128_2010_112

    Google Scholar 

  83. Zhu T, Boons GJ (2001) Org Lett 3:4201

    Article  CAS  Google Scholar 

  84. Crich D, Jayalath P (2005) J Org Chem 70:7252

    Article  CAS  Google Scholar 

  85. Crich D, Subrammanian V, Hutton TK (2007) Tetrahedron 63:5042

    Article  CAS  Google Scholar 

  86. Crich D, Sharma I (2008) Org Lett 10:4731

    Article  CAS  Google Scholar 

  87. Martichonok V, Whitesides GM (1996) J Org Chem 61:1702

    Article  CAS  Google Scholar 

  88. Sliedregt LAJM, van der Marel GA, van Boom JH (1994) Tetrahedron Lett 35:4015

    Article  CAS  Google Scholar 

  89. Yan L, Kahne D (1996) J Am Chem Soc 118:9239

    Article  CAS  Google Scholar 

  90. Thompson C, Ge M, Kahne D (1999) J Am Chem Soc 121:1237

    Article  CAS  Google Scholar 

  91. Kim KS, Kim JH, Lee YJ, Lee YJ, Park J (2001) J Am Chem Soc 123:8477

    Article  CAS  Google Scholar 

  92. Kim KS, Seo YS, Kim HJ, Lee YJ, Jeong K-S (2003) Synlett 9:1311

    Article  Google Scholar 

  93. Kim KS, Park J, Lee YJ, Seo YS (2003) Angew Chem Int Ed 42:459

    Article  CAS  Google Scholar 

  94. Kwon YT, Lee YJ, Lee K, Kim KS (2004) Org Lett 6:3901

    Article  CAS  Google Scholar 

  95. Lee YJ, Lee K, Jung EH, Jeon HB, Kim KS (2005) Org Lett 7:3263

    Article  CAS  Google Scholar 

  96. Lee YJ, Lee B-Y, Jeon HB, Kim KS (2006) Org Lett 8:3971

    Article  CAS  Google Scholar 

  97. Lee YJ, Baek JY, Lee B-Y, Kang SS, Park H-S, Jeon HB, Kim KS (2006) Carbohydr Res 341:1708

    Article  CAS  Google Scholar 

  98. Lee BR, Jeon JM, Jung JH, Jeon HB, Kim KS (2006) Can J Chem 84:506

    Article  CAS  Google Scholar 

  99. Fulse DB, Jeon HB, Kim KS (2007) J Org Chem 72:9963

    Article  CAS  Google Scholar 

  100. Kim KS, Jeon HB (2007) ACS Symp Ser 960:134

    Article  CAS  Google Scholar 

  101. Kim KS, Suk DH (2011) Effect of electron-withdrawing protecting groups at remote positions of donors on glycosylation stereochemistry. In: Topics in current chemistry. Springer, Heidelberg. doi:10.1007/128_2010_107

    Google Scholar 

  102. Crich D (2010) Acc Chem Res 43:1144

    Article  CAS  Google Scholar 

  103. Sajiki H (1995) Tetrahedron Lett 36:3465

    Article  CAS  Google Scholar 

  104. Aubry S, Sasaki K, Sharma I, Crich D (2011) Influence of protecting groups on the reactivity and selectivity of glycosylation: chemistry of the 4,6-O-benzylidene protected mannopyranosyl donors and related species. In: Topics in current chemistry. Springer, Heidelberg. doi: 10.1007/128_2010_102

    Google Scholar 

  105. Huang L, Wang Z, Huang X (2004) Chem Commun 1960

    Google Scholar 

  106. Li X, Huang L, Hu X, Huang X (2009) Org Biomol Chem 7:117

    Article  CAS  Google Scholar 

  107. Cura P, Aloui M, Kartha KPR, Field RA (2000) Synlett 9:1279

    Google Scholar 

  108. Tatai J, Fügedi P (2007) Org Lett 9:4647

    Article  CAS  Google Scholar 

  109. Crich D, Cai F, Yang F (2008) Carbohydr Res 343:1858

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC). RR is especially grateful to the many coworkers, graduate students, and postdoctoral fellows, past and present, who have significantly contributed to his research activities and to NSERC and UQAM for generous supports through a Canadian Research Chair in Therapeutic Chemistry.

Author information

Authors and Affiliations

  1. Pharmaqam – Groupe de Recherche en Chimie Thérapeutique, Université du Québec à Montréal, 8888, Succ. Centre-ville, Montréal, QC, Canada, H3C 3P8

    Tze Chieh Shiao & René Roy

Authors
  1. Tze Chieh Shiao
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. René Roy
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to René Roy .

Editor information

Editors and Affiliations

  1. Natural Products and Glycotechnology Res, Swarthmore Road 4118, Durham, 27706, North Carolina, USA

    Bert Fraser-Reid

  2. Instituto de Quimica Orgánica General (C, Juan de la Cierva 3, Madrid, 28006, Spain

    J. Cristóbal López

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Shiao, T.C., Roy, R. (2010). “Active–Latent” Thioglycosyl Donors and Acceptors in Oligosaccharide Syntheses. In: Fraser-Reid, B., Cristóbal López, J. (eds) Reactivity Tuning in Oligosaccharide Assembly. Topics in Current Chemistry, vol 301. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2010_108

Download citation

Publish with us

Policies and ethics

Search

Navigation