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Anomeric Anhydro Sugars

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Glycoscience

Abstract

Anomeric anhydro sugars are sugar derivatives where the anomeric carbon participates in an acetal linkage with two of the hydroxyl groups of the sugar. They are essentially intramolecular glycosides, and their bicyclic nature provides a powerful conformational constraint that greatly influences their reactivity. This chapter reviews the occurrence, properties, formation, and reactions of anomeric anhydro sugars. Particular emphasis is placed on 1,2- and 1,6‑anhydropyranoses, including conformational aspects and ring‐opening reactions. Epoxide‐containing 1,6‑anhydro sugars (Černý epoxides) are briefly reviewed, and the formation and some reactions of the 1,6‑anhydro sugar enone, levoglucosenone, is covered. An overview is given of the use of 1,2‑anhydro sugar as glycosyl donors. Also discussed are the formation and reactions of anomeric anhydro sugars containing nitrogen, sulfur, or selenium.

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Abbreviations

CSA:

camphorsulfonic acid

DMDO:

3,3‑dimethyldioxirane

mw:

microwave

NIS:

N‑iodosuccinimide

TESOTf:

triethylsilyl triflate

References

  1. Angyal SJ, Dawes K (1968) Aust J Chem 21:2747

    Article  CAS  Google Scholar 

  2. Kochetkov NK (1987) Tetrahedron 43:2389

    Article  CAS  Google Scholar 

  3. Černý M, Stanek J Jr (1977) Adv Carbohydr Chem Biochem 34:23

    Article  Google Scholar 

  4. Bols M (1996) 1,6‑Anhydro sugars. Carbohydrate building blocks. Wiley, New York

    Google Scholar 

  5. Peat S (1946) Adv Carbohydr Chem 2:37

    Google Scholar 

  6. Witczak ZJ (1994) Selective protection of levoglucosan derivatives. In: Witczak ZJ (ed) Frontiers in biomedicine and biotechnology. Levoglucosenone and levoglucosans, chemistry and applications. ATL Press, Mount Prospect, 2:165

    Google Scholar 

  7. Tanret M (1894) Bull Soc Chim Fr 211:944

    Google Scholar 

  8. Park YJ, Kim HS, Jeffrey GA (1971) Acta Cryst B 27:220

    Article  CAS  Google Scholar 

  9. Heyns K, Weyer J (1968) Liebigs Ann Chem 718:224

    Article  CAS  Google Scholar 

  10. Pictet A, Sarasin J (1918) Helv Chim Acta 1:87

    Article  Google Scholar 

  11. Ward RB (1963) Methods Carbohydr Chem 2:394

    Google Scholar 

  12. Shafizadeh F, Furneaux RH, Stevenson TT, Cochran TG (1978) Carbohydr Res 61:519

    Article  CAS  Google Scholar 

  13. Schkolnik G, Rudich Y (2006) Anal Bioanal Chem 385:26

    Article  CAS  Google Scholar 

  14. Knauf AE, Hann RM, Hudson CS (1941) J Am Chem Soc 63:1447

    Article  CAS  Google Scholar 

  15. Hann RM, Hudson CS (1942) J Am Chem Soc 64:925

    Article  CAS  Google Scholar 

  16. Zottola MA, Alonso R, Vite GD, Fraser-Reid B (1989) J Org Chem 54:6123

    Article  CAS  Google Scholar 

  17. Cleophax J (2003) Synthesis 1015

    Google Scholar 

  18. Coleman GH (1963) Methods Carbohydr Chem 2:397

    Google Scholar 

  19. Boons G-J, Isles S, Setälä P (1995) Synlett 755

    Google Scholar 

  20. Rao MV, Nagarajan M (1987) Carbohydr Res 162:141

    Article  CAS  Google Scholar 

  21. Caron S, McDonald A, Heathcock CH (1996) Carbohydr Res 281:179

    Article  CAS  Google Scholar 

  22. Haeckel R, Lauer G, Oberdorfer F (1996) Synlett 21

    Google Scholar 

  23. Mereyala HB, Venkataramanaiah KC, Dalvoy VS (1992) Carbohydr Res 225:151

    Article  CAS  Google Scholar 

  24. Lauer G, Oberdorfer F (1993) Angew Chem Int Ed Engl 32:272

    Article  Google Scholar 

  25. Černý M (1994) 1,6:2,3- and 1,6:3,4‑Dianhydro‐β‑d‑hexopyranoses. Synthesis and preparative applications. In: Witczak ZJ (ed) Frontiers in biomedicine and biotechnology. Levoglucosenone and levoglucosans, chemistry and applications. ATL Press, Mount Prospect, 2:121

    Google Scholar 

  26. Tailler D, Jacquinet JC, Noirot AM, Beau JM (1992) J Chem Soc Perkin 1 3163

    Google Scholar 

  27. Černý M (2003) Adv Carbohydr Chem Biochem 58:122

    Google Scholar 

  28. Stoffyn PJ, Jeanloz RW (1960) J Biol Chem 235:2507

    CAS  Google Scholar 

  29. Hölte JV (1998) Microbiol Mol Biol R 62:181

    Google Scholar 

  30. Hölte JV, Mirelman D, Sharon N, Schwarz U (1975) J Bacteriol 124:1067

    Google Scholar 

  31. Uehara T, Suefuji K, Valbuena N, Meehan B, Donegan M, Park J (2005) J Bacteriol 187:3643

    Article  CAS  Google Scholar 

  32. Pulido R, Gotor V (1994) Carbohydr Res 252:55

    CAS  Google Scholar 

  33. Ljunger G, Adlercreutz P, Mattiasson B (1994) Biotechnol Lett 16:1167

    Article  CAS  Google Scholar 

  34. Somsák L, Ferrier RJ (1991) Adv Carbohydr Chem Biochem 49:37

    Article  Google Scholar 

  35. Ohrui H, Horiki H, Kishi H, Meguro H (1983) Agric Biol Chem 47:1101

    CAS  Google Scholar 

  36. Ferrier RJ, Furneaux RH (1980) Aust J Chem 33:1025

    Article  CAS  Google Scholar 

  37. Nishikawa T, Mishima Y, Ohyabu N, Isobe M (2004) Tetrahedron Lett 45:175

    Article  CAS  Google Scholar 

  38. Vogel C, Liebelt B, Steffan W, Kristen H (1992) J Carbohydr Chem 11:287

    Article  CAS  Google Scholar 

  39. Zottola M, Rao BV, Fraser-Reid B (1991) J Chem Soc Chem Commun 969

    Google Scholar 

  40. Lee JC, Tai CA, Hung SC (2002) Tetrahedron Lett 43:851

    Article  CAS  Google Scholar 

  41. Burgey CS, Vollerthun R, Fraser-Reid B (1994) Tetrahedron Lett 35:2637

    Article  CAS  Google Scholar 

  42. Wang L-X, Sakairi N, Kuzuhara H (1990) J Chem Soc Perkin 1 1677

    Google Scholar 

  43. Koto S, Uchida T, Zen S (1972) Chem Lett 1049

    Google Scholar 

  44. Ruckel ER, Schuerch C (1966) J Org Chem 31:2233

    Article  CAS  Google Scholar 

  45. Yoshida T, Nakashima H, Yamamoto N, Uryu T (1993) Polymer J 25:1069

    Article  CAS  Google Scholar 

  46. Brigl P (1922) Hoppe-Seyler's Z Physiol Chem 122:245

    Article  CAS  Google Scholar 

  47. Lemieux RU, Huber G (1956) J Am Chem Soc 78:4117

    Article  CAS  Google Scholar 

  48. Halcomb RL, Danishefsky SJ (1989) J Am Chem Soc 111:6661

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  50. Collins P, Ferrier R (1995) Monosaccharides: Their Chemistry and Their Roles in Natural Products. Wiley, Chichester

    Google Scholar 

  51. Leeuwenburgh MA, van der Marel GA, Overkleeft HS, van Boom JH (2003) J Carbohydr Chem 22:549

    Article  CAS  Google Scholar 

  52. Timmers CM, Wigchert SCM, Leeuwenburgh MA, van der Marel GA, van Boom JH (1998) Eur J Org Chem 1998:91

    Article  Google Scholar 

  53. Seeberger PH, Danishefsky SJ (1998) Acc Chem Res 31:685

    Article  CAS  Google Scholar 

  54. Ito H, Eby R, Kramer S, Schuerch C (1980) Carbohydr Res 86:193

    Article  CAS  Google Scholar 

  55. Bhagwat SS, Hamam PR, Still WC (1985) J Am Chem Soc 107:6372

    Article  CAS  Google Scholar 

  56. Kops J, Schuerch C (1965) J Org Chem 30:3951

    Article  CAS  Google Scholar 

  57. Bullock C, Hough L, Richardson AC (1990) Carbohydr Res 197:131

    Article  CAS  Google Scholar 

  58. Thiem J, Wiesner M (1993) Carbohydr Res 249:197

    Article  Google Scholar 

  59. Nokami T, Werz DB, Seeberger PH (2005) Helv Chim Acta 88:2823

    Article  CAS  Google Scholar 

  60. Dimler RJ, Davis HA, Hilbert GE (1946) J Am Chem Soc 68:1377

    Article  CAS  Google Scholar 

  61. Alexander BH, Dimler RJ, Mehltretter CL (1951) J Am Chem Soc 73:4658

    Article  CAS  Google Scholar 

  62. Dimler RJ (1952) Adv Carbohydr Chem 7:37

    CAS  Google Scholar 

  63. Angyal SJ, Beveridge RJ (1978) Aust J Chem 31:1151

    Article  CAS  Google Scholar 

  64. Sarkar SK, Choudhury AK, Mukhopadhyay B, Roy N (1999) J Carbohydr Chem 18:1121

    Article  CAS  Google Scholar 

  65. Witczak ZJ (1994) Levoglucosenone; past, present and further applications In: Witczak ZJ (ed) Frontiers in biomedicine and biotechnology. Levoglucosenone and levoglucosans, chemistry and applications. ATL Press, Mount Prospect, 2:3

    Google Scholar 

  66. Halpern Y, Riffer R, Broido A (1973) J Org Chem 38:204

    Article  CAS  Google Scholar 

  67. Shafizadeh F, Furneaux RH, Stevenson TT (1979) Carbohydr Res 71:169

    Article  CAS  Google Scholar 

  68. Brimacombe JS, Hunedy F, Tucker LCN (1978) Carbohydr Res 60:C11

    Article  CAS  Google Scholar 

  69. Shafizadeh F, Chin PPS (1977) Carbohydr Res 58:79

    Article  CAS  Google Scholar 

  70. Mori M, Chuman T, Kato K (1984) Carbohydr Res 129:73

    Article  CAS  Google Scholar 

  71. Witczak ZJ (1994) Pure Appl Chem 66:2189

    Article  CAS  Google Scholar 

  72. Witczak ZJ, Chhabra R, Chen H, Xie X-Q (1997) Carbohydr Res 301:167

    Article  CAS  Google Scholar 

  73. Ward DD, Shafizadeh F (1981) Carbohydr Res 95:155

    Article  CAS  Google Scholar 

  74. Akagi M, Tejima S, Haga M (1963) Chem Pharm Bull 11:58

    CAS  Google Scholar 

  75. Lundt I, Skelbæk-Pedersen B (1981) Acta Chem Scand B35:637

    Article  CAS  Google Scholar 

  76. Whistler RL, Seib PA (1966) Carbohydr Res 2:93

    Article  CAS  Google Scholar 

  77. Driguez H, McAuliffe JC, Stick RV, Tilbrook DMG, Williams SJ (1996) Aust J Chem 49:343

    Article  CAS  Google Scholar 

  78. Ramesha AR, Chandrasekaran S (1992) Synth Commun 22:3227

    Article  Google Scholar 

  79. Sridhar PR, Saravanan V, Chandrasekaran S (2005) Pure Appl Chem 77:145

    Article  CAS  Google Scholar 

  80. Yamamoto K, Haga M, Tejima S (1975) Chem Pharm Bull 23:233

    CAS  Google Scholar 

  81. Skelton BW, Stick RV, Tilbrook DMG, White AH, Williams SJ (2000) Aust J Chem 53:389

    Article  CAS  Google Scholar 

  82. Stick RV, Tilbrook DMG, Williams SJ (1997) Tetrahedron Lett 38:2741

    Article  CAS  Google Scholar 

  83. Stick RV, Tilbrook DMG, Williams SJ (1999) Aust J Chem 52:685

    Article  CAS  Google Scholar 

  84. Buděšínský M, Poláková J, Hamerníková M, Císařová I, Trnka TS, Černý M (2006) Coll Czech Chem Commun 71:311

    Article  Google Scholar 

  85. Paulsen H, Todt K (1967) Chem Ber 100:512

    Article  CAS  Google Scholar 

  86. Lafont D, Wollny A, Boullanger P (1998) Carbohydr Res 310:9

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. School of Chemistry, The University of Melbourne, Parkville, VIC, 3052, Australia

    Nathan W. McGill & Spencer J. Williams

Authors
  1. Nathan W. McGill
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  2. Spencer J. Williams
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Corresponding author

Correspondence to Spencer J. Williams .

Editor information

Editors and Affiliations

  1. Natural Products and Glycotechnology Research Institute Inc., North Caroline State University, 4118 Swarthmore Road, Durham, NC, 27707, USA

    Bertram O. Fraser-Reid Prof. Dr.

  2. University Graduate School of Science and Engineering, 3-4-1 Ohkubo, Shinjuku, Tokyo, Japan

    Kuniaki Tatsuta Prof. Dr.

  3. Faculty of ScienceDepartment of Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany

    Joachim Thiem Prof. Dr.

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McGill, N., Williams, S. (2008). Anomeric Anhydro Sugars. In: Fraser-Reid, B.O., Tatsuta, K., Thiem, J. (eds) Glycoscience. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30429-6_16

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