562
3
Chemical Glycosylation Reactions
lipoarabinomannan, found in the mycobacterial cell wall, was also synthesized by employing
the latent (BCB)-active (CB) glycosylation method ( > Scheme 81) [93]. Very recently, they
reported the total synthesis of agelagalastatin, which is a trisaccharide sphingolipid and displays significant in vitro inhibitory activities against human cancer cell growth [96]. Among
three glycosyl linkages in agelagalastatin, α-galactofuranosyl and β-galactofuranosyl linkages
were stereoselectively constructed employing the CB glycoside method ( > Scheme 82) [97].
On the other hand, they reported the glycosylation of various acceptors with glycosyl benzyl
phthalates as glycosyl donors using TMSOTf as the promoter ( > Scheme 83) [98].
References
1. Helferich B, Shimitz-Hillebrecht E (1933) Chem
Ber 66:378
2. Boivin J, Monneret C, Pais M (1978) Tetrahedron
Lett 19:1111
3. Lemieux RU, Shyluk WP (1953) Can J Chem
31:528
4. Hanessian S, Banoub J (1977) Carbohydr Res
59:261
5. Honma K, Nakazima K, Uematsu T, Hamada A
(1976) Chem Pharm Bull 24:394
6. Dayal B, Salen G, Padia J, Shefer S, Tint GS,
Sasso G, Williams TH (1993) Carbohydr Res
240:133
7. Benjahad A, Benhaddou R, Granet R, Kaouadji
M, Krausz P, Piekarski S, Thomasson F, Bosgiraud C, Delebassée S (1994) Tetrahedron Lett
35:9545
8. Gaud O, Granet R, Kaouadji M, Krausz P, Blais
JC, Bolbach G (1996) Can J Chem 74:481
9. Kiso M, Anderson L (1979) Carbohydr Res
72:C15
10. Lerner LM (1990) Carbohydr Res 207:138
11. Katsuraya K, Ikushima N, Takahashi N, Shoji T,
Nakashima H, Yamamoto N, Yoshida T, Uryu T
(1994) Carbohydr Res 260:51
12. Chatterjee SK, Nuhn P (1998) Chem Commun
1729
13. Dahmén J, Frejd T, Magnusson G, Noori G (1983)
Carbohydr Res 114:328
14. Gurjar MK, Viswanadham G (1991) Tetrahedron
Lett 32:6191
15. Elofsson M, Walse B, Kihlberg J (1991) Tetrahedron Lett 32:7613
16. Steffan W, Schutkowski M, Fischer G (1996)
J Chem Soc Chem Commun 313
17. Gangadhar BP, Jois SDS, Balasubramaniam A
(2004) Tetrahedron Lett 45:355
18. Wang TC, Furukawa H, Nihro Y, Kakegawa H,
Matsumoto H, Satoh T (1994) Chem Pharm Bull
42:570
19. (a) Ludin C, Weller T, Seitz B, Meier W, Erbeck
S, Hoenke C, Krieger R, Keller M, Knothe L, Pelz
K, Wittmer A, Prinzbach H (1995) Liebigs Ann
291;
(b) Erbeck S, Prinzbach H (1997) Tetrahedron
Lett 38:2653;
(c) Erbeck S, Liang X, Hunkler D, Krieger R,
Prinzbach H (1998) Eur J Org Chem 1935
20. Lam SN, Gervay-Hague J (2005) J Org Chem
70:8772
21. Kelly NM, Jensen KJ (2001) J Carbohydr Chem
20:537
22. Ikeda K, Torisawa Y, Nishi T, Minamikawa J,
Tanaka, K, Sato M (2003) Bioorg Med Chem
11:3073
23. Ogawa T, Beppu K, Nakabayashi S (1981) Carbohydr Res 93:C6
24. Ogawa T, Beppu K (1982) Carbohydr Res
101:271
25. (a) Kovac P (1986) Carbohydr Res 153:237;
(b) PozsgayV, Brisson JR, Jennings HJ (1987)
Can J Chem 65:2764;
(c) Pozsgay V, Brisson JR, Jennings HJ (1990)
Carbohydr Res 205:133;
(d) Nifant’ev NE, Lipkind GM, Shashkov
AS, Kochetkov NK (1992) Carbohydr Res
223:109
26. Nifant’ev NE, Backinowsky LV, Kochetkov NK
(1988) Carbohydr Res 174:61
27. Nifant’ev NE, Khatuntseva EA, Shashkov AS,
Bock K (1996) Carbohydr Lett 1:399
28. Trumtel M, Tavecchia P, Veyriéres A, Sinaÿ P
(1989) Carbohydr Res 191:29
29. Paulsen H, Paal M (1984) Carbohydr Res 135:53
30. Paulsen H, Tietz H (1985) Angew Chem Int Ed
Engl 24:128
31. Pozsgay V, Brisson JR, Jennings HJ (1991) J Org
Chem 56:3377
32. Rainer H, Scharf HD, Runsink J (1992) Liebigs
Ann Chem 103
3
Chemical Glycosylation Reactions
lipoarabinomannan, found in the mycobacterial cell wall, was also synthesized by employing
the latent (BCB)-active (CB) glycosylation method ( > Scheme 81) [93]. Very recently, they
reported the total synthesis of agelagalastatin, which is a trisaccharide sphingolipid and displays significant in vitro inhibitory activities against human cancer cell growth [96]. Among
three glycosyl linkages in agelagalastatin, α-galactofuranosyl and β-galactofuranosyl linkages
were stereoselectively constructed employing the CB glycoside method ( > Scheme 82) [97].
On the other hand, they reported the glycosylation of various acceptors with glycosyl benzyl
phthalates as glycosyl donors using TMSOTf as the promoter ( > Scheme 83) [98].
References
1. Helferich B, Shimitz-Hillebrecht E (1933) Chem
Ber 66:378
2. Boivin J, Monneret C, Pais M (1978) Tetrahedron
Lett 19:1111
3. Lemieux RU, Shyluk WP (1953) Can J Chem
31:528
4. Hanessian S, Banoub J (1977) Carbohydr Res
59:261
5. Honma K, Nakazima K, Uematsu T, Hamada A
(1976) Chem Pharm Bull 24:394
6. Dayal B, Salen G, Padia J, Shefer S, Tint GS,
Sasso G, Williams TH (1993) Carbohydr Res
240:133
7. Benjahad A, Benhaddou R, Granet R, Kaouadji
M, Krausz P, Piekarski S, Thomasson F, Bosgiraud C, Delebassée S (1994) Tetrahedron Lett
35:9545
8. Gaud O, Granet R, Kaouadji M, Krausz P, Blais
JC, Bolbach G (1996) Can J Chem 74:481
9. Kiso M, Anderson L (1979) Carbohydr Res
72:C15
10. Lerner LM (1990) Carbohydr Res 207:138
11. Katsuraya K, Ikushima N, Takahashi N, Shoji T,
Nakashima H, Yamamoto N, Yoshida T, Uryu T
(1994) Carbohydr Res 260:51
12. Chatterjee SK, Nuhn P (1998) Chem Commun
1729
13. Dahmén J, Frejd T, Magnusson G, Noori G (1983)
Carbohydr Res 114:328
14. Gurjar MK, Viswanadham G (1991) Tetrahedron
Lett 32:6191
15. Elofsson M, Walse B, Kihlberg J (1991) Tetrahedron Lett 32:7613
16. Steffan W, Schutkowski M, Fischer G (1996)
J Chem Soc Chem Commun 313
17. Gangadhar BP, Jois SDS, Balasubramaniam A
(2004) Tetrahedron Lett 45:355
18. Wang TC, Furukawa H, Nihro Y, Kakegawa H,
Matsumoto H, Satoh T (1994) Chem Pharm Bull
42:570
19. (a) Ludin C, Weller T, Seitz B, Meier W, Erbeck
S, Hoenke C, Krieger R, Keller M, Knothe L, Pelz
K, Wittmer A, Prinzbach H (1995) Liebigs Ann
291;
(b) Erbeck S, Prinzbach H (1997) Tetrahedron
Lett 38:2653;
(c) Erbeck S, Liang X, Hunkler D, Krieger R,
Prinzbach H (1998) Eur J Org Chem 1935
20. Lam SN, Gervay-Hague J (2005) J Org Chem
70:8772
21. Kelly NM, Jensen KJ (2001) J Carbohydr Chem
20:537
22. Ikeda K, Torisawa Y, Nishi T, Minamikawa J,
Tanaka, K, Sato M (2003) Bioorg Med Chem
11:3073
23. Ogawa T, Beppu K, Nakabayashi S (1981) Carbohydr Res 93:C6
24. Ogawa T, Beppu K (1982) Carbohydr Res
101:271
25. (a) Kovac P (1986) Carbohydr Res 153:237;
(b) PozsgayV, Brisson JR, Jennings HJ (1987)
Can J Chem 65:2764;
(c) Pozsgay V, Brisson JR, Jennings HJ (1990)
Carbohydr Res 205:133;
(d) Nifant’ev NE, Lipkind GM, Shashkov
AS, Kochetkov NK (1992) Carbohydr Res
223:109
26. Nifant’ev NE, Backinowsky LV, Kochetkov NK
(1988) Carbohydr Res 174:61
27. Nifant’ev NE, Khatuntseva EA, Shashkov AS,
Bock K (1996) Carbohydr Lett 1:399
28. Trumtel M, Tavecchia P, Veyriéres A, Sinaÿ P
(1989) Carbohydr Res 191:29
29. Paulsen H, Paal M (1984) Carbohydr Res 135:53
30. Paulsen H, Tietz H (1985) Angew Chem Int Ed
Engl 24:128
31. Pozsgay V, Brisson JR, Jennings HJ (1991) J Org
Chem 56:3377
32. Rainer H, Scharf HD, Runsink J (1992) Liebigs
Ann Chem 103