694
3
Chemical Glycosylation Reactions
In > Scheme 67 is shown the assembly of the thio analogue of a phytoelicitor active heptasaccharide. In contrast to the above example, here all the thio-interglycosidic linkages are formed
through the reaction of anomeric thiols with non-anomeric electrophiles [196].
In spite of the difference in methodology between these syntheses, both are impressive and
excellent representatives of the state of the art of thiooligosaccharide synthesis.
References
1. Horton D, Hutson DH (1963) Adv Carbohydr
Chem 18:123
2. Gil V, MacLeod AJ (1980) Phytochemistry
19:2071
3. Fahey JW, Zalcmann AT, Talalay P (2001) Phytochemistry 56:5
4. Herr RR (1967) J Am Chem Soc 89:2444
5. Hoeksema H, Bannister B, Birkenmeyer RD,
Kagan F, Magerlein BJ, MacKellar FA, Schroeder W, Slomp G, Herr RR (1964) J Am Chem Soc
86:4223
6. Hoeksema H (1964) J Am Chem Soc 86:4224
7. Ngane AN, Lavault M, Seraphin D, Landreau A,
Richomme P (2006) Carbohydr Res 341:2799
8. Khiar N, Suarez B, Valdivia V, Fernandez I
(2005) Synlett 19:2963
9. Khiar N, Araujo CS, Suarez B, Fernandez I
(2006) Eur J Org Chem 7:1685
10. Bundle DR, Rich JR, Jacques S, Yu HN, Nitz M,
Ling C-C (2005) Angew Chem Int Ed 44:7725
11. Norberg T (1996) In: Khan SH, O’Neill RA
(eds) Modern Methods in Carbohydrate Synthesis. Harwood, London, p 82
12. Garegg PJ (1997) Adv Carbohydr Chem
Biochem 52:179
13. Oscarson S (2000) In: Ernst B, Hart G, Sinaÿ P
(eds) Oligosaccharides in Chemistry and Biology: A Comprehensive Handbook. Wiley-VCH,
Weinheim
14. Kartha KPR, Field RA (2003) In: Osborn
HMI (ed) Carbohydrates. Elsevier Science Ltd,
Oxford, p 121
15. Defaye J, Gelas J (1991) In: Atta-ur-Rahman (ed) Studies in Natural Products Chemistry,
vol 8 E. Elsevier, Amsterdam, p 315
16. Defaye J (1995) In: Petersen SB, Svensson B,
Petersen S (eds) Progress in Biotechnology, vol
10. Elsevier, Amsterdam, p 113
17. Driguez H (1997) Topics Curr Chem 187:85
18. Fairweather JK, Driguez H (2000) In: Ernst
B, Hart G, Sinaÿ P (eds) Oligosaccharides
in Chemistry and Biology: A Comprehensive
Handbook. Wiley-VCH, Weinheim, p 531
19. Kahne D, Walker S, Cheng Y, van Engen D
(1989) J Am Chem Soc 111:6881
20. Crich D, Lim LBL (2004) Org React 64:115
21. Agnihotri G, Misra AK (2005) Tetrahedron Lett
46:8113
22. Fernandez I, Khiar N (2003) Chem Rev
103:3651
23. Mehta S, Pinto BM (1991) Tetrahedron Lett
32:4435
24. Mehta S, Pinto BM (1996) In: Khan SH, O’Neill
RA (eds) Modern Methods in Carbohydrate
Synthesis. Harwood, London, p 107
25. van Well RM, Kaerkkaeinen TS, Kartha KPR,
Field RA (2006) Carbohydr Res 341:1391
26. Buts L, Bouckaert J, De Genst E, Loris R, Oscarson S, Lahmann M, Messens J, Brosens E, Wyns
L, De Greve H (2003) Acta Cryst D 59:1012
27. Cioci G, Mitchell EP, Chazalet V, Debray H,
Oscarson S, Lahmann M, Breton C, Gautier C,
Perez S, Imberty A (2006) J Mol Biol 357:1575
28. Witczak ZJ, Czernecki S (1998) Adv Carbohydr
Chem Biochem 53:143
29. Robina I, Vogel P, Witczak ZJ (2001) Curr Org
Chem 5:1177
30. Brigl P, Schinle R (1932) Ber dtsch chem Ges
65:1890
31. Lemieux RU (1951) Can J Chem 29:1079
32. Lemieux RU, Brice C (1955) Can J Chem
33:109
33. Hough L, Taha MI (1956) J Chem Soc 2042
34. Ferrier RJ, Furneaux RH (1976) Carbohydr Res
52:63
35. Das SK, Roy N (1996) Carbohydr Res 296:275
36. Dasgupta F, Garegg PJ (1989) Acta Chem Scand
43:471
37. Contour M-O, Defaye J, Little M, Wong E
(1989) Carbohydr Res 193:283
38. Das SK, Roy J, Reddy KA, Abbineni C (2003)
Carbohydr Res 338:2237
39. Weng S-S, Lin Y-D, Chen C-T (2006) Org Lett
8:5633
40. Vesely J, Ledvina M, Jindrich J, Saman D, Trnka
T (2003) Collect Czech Chem Comm 68: 1264
3
Chemical Glycosylation Reactions
In > Scheme 67 is shown the assembly of the thio analogue of a phytoelicitor active heptasaccharide. In contrast to the above example, here all the thio-interglycosidic linkages are formed
through the reaction of anomeric thiols with non-anomeric electrophiles [196].
In spite of the difference in methodology between these syntheses, both are impressive and
excellent representatives of the state of the art of thiooligosaccharide synthesis.
References
1. Horton D, Hutson DH (1963) Adv Carbohydr
Chem 18:123
2. Gil V, MacLeod AJ (1980) Phytochemistry
19:2071
3. Fahey JW, Zalcmann AT, Talalay P (2001) Phytochemistry 56:5
4. Herr RR (1967) J Am Chem Soc 89:2444
5. Hoeksema H, Bannister B, Birkenmeyer RD,
Kagan F, Magerlein BJ, MacKellar FA, Schroeder W, Slomp G, Herr RR (1964) J Am Chem Soc
86:4223
6. Hoeksema H (1964) J Am Chem Soc 86:4224
7. Ngane AN, Lavault M, Seraphin D, Landreau A,
Richomme P (2006) Carbohydr Res 341:2799
8. Khiar N, Suarez B, Valdivia V, Fernandez I
(2005) Synlett 19:2963
9. Khiar N, Araujo CS, Suarez B, Fernandez I
(2006) Eur J Org Chem 7:1685
10. Bundle DR, Rich JR, Jacques S, Yu HN, Nitz M,
Ling C-C (2005) Angew Chem Int Ed 44:7725
11. Norberg T (1996) In: Khan SH, O’Neill RA
(eds) Modern Methods in Carbohydrate Synthesis. Harwood, London, p 82
12. Garegg PJ (1997) Adv Carbohydr Chem
Biochem 52:179
13. Oscarson S (2000) In: Ernst B, Hart G, Sinaÿ P
(eds) Oligosaccharides in Chemistry and Biology: A Comprehensive Handbook. Wiley-VCH,
Weinheim
14. Kartha KPR, Field RA (2003) In: Osborn
HMI (ed) Carbohydrates. Elsevier Science Ltd,
Oxford, p 121
15. Defaye J, Gelas J (1991) In: Atta-ur-Rahman (ed) Studies in Natural Products Chemistry,
vol 8 E. Elsevier, Amsterdam, p 315
16. Defaye J (1995) In: Petersen SB, Svensson B,
Petersen S (eds) Progress in Biotechnology, vol
10. Elsevier, Amsterdam, p 113
17. Driguez H (1997) Topics Curr Chem 187:85
18. Fairweather JK, Driguez H (2000) In: Ernst
B, Hart G, Sinaÿ P (eds) Oligosaccharides
in Chemistry and Biology: A Comprehensive
Handbook. Wiley-VCH, Weinheim, p 531
19. Kahne D, Walker S, Cheng Y, van Engen D
(1989) J Am Chem Soc 111:6881
20. Crich D, Lim LBL (2004) Org React 64:115
21. Agnihotri G, Misra AK (2005) Tetrahedron Lett
46:8113
22. Fernandez I, Khiar N (2003) Chem Rev
103:3651
23. Mehta S, Pinto BM (1991) Tetrahedron Lett
32:4435
24. Mehta S, Pinto BM (1996) In: Khan SH, O’Neill
RA (eds) Modern Methods in Carbohydrate
Synthesis. Harwood, London, p 107
25. van Well RM, Kaerkkaeinen TS, Kartha KPR,
Field RA (2006) Carbohydr Res 341:1391
26. Buts L, Bouckaert J, De Genst E, Loris R, Oscarson S, Lahmann M, Messens J, Brosens E, Wyns
L, De Greve H (2003) Acta Cryst D 59:1012
27. Cioci G, Mitchell EP, Chazalet V, Debray H,
Oscarson S, Lahmann M, Breton C, Gautier C,
Perez S, Imberty A (2006) J Mol Biol 357:1575
28. Witczak ZJ, Czernecki S (1998) Adv Carbohydr
Chem Biochem 53:143
29. Robina I, Vogel P, Witczak ZJ (2001) Curr Org
Chem 5:1177
30. Brigl P, Schinle R (1932) Ber dtsch chem Ges
65:1890
31. Lemieux RU (1951) Can J Chem 29:1079
32. Lemieux RU, Brice C (1955) Can J Chem
33:109
33. Hough L, Taha MI (1956) J Chem Soc 2042
34. Ferrier RJ, Furneaux RH (1976) Carbohydr Res
52:63
35. Das SK, Roy N (1996) Carbohydr Res 296:275
36. Dasgupta F, Garegg PJ (1989) Acta Chem Scand
43:471
37. Contour M-O, Defaye J, Little M, Wong E
(1989) Carbohydr Res 193:283
38. Das SK, Roy J, Reddy KA, Abbineni C (2003)
Carbohydr Res 338:2237
39. Weng S-S, Lin Y-D, Chen C-T (2006) Org Lett
8:5633
40. Vesely J, Ledvina M, Jindrich J, Saman D, Trnka
T (2003) Collect Czech Chem Comm 68: 1264