Glycosyl Halides
3.1
447
⊡ Scheme 38
Following the extensive studies using a heterogeneous and reusable solid catalyst in a glycosylation reaction by Toshima et al. for greening the chemical glycosylation method [74], the
use of an ionic liquid as an environmentally benign reaction media for the glycosylation of
glycosyl fluoride was reported by Toshima et al. [81]. In this study, it was demonstrated not
only the reusability of the ionic liquid in the glycosylation reaction but also the potency of the
ionic liquid for stereocontrol of the glycosylation reaction ( > Scheme 38).
References
1. Koenigs W, Knorr E (1901) Chem Ber 34:957
2. Lemieux RU, Hayami JI (1965) Can J Chem
43:2162
3. (a) Paulsen H, Lockhoff O (1981) Chem Ber
114:3102; (b) Paulsen H, Kutschker W, Lockhoff
O (1981) Chem Ber 114:3233
4. (a) Wulff G, Röhle G (1974) Angew Chem
Int Ed Engl 13:157; (b) Bochkov A-F, Zaikov
GE (1979) (eds) Chemistry of the O-Glycosidic
Bond: Formation and Cleavage. Pergamon Press,
Oxford; (c) Tsutsumi H, Ishido Y (1980)
J Synth Org Chem Jpn 38:473; (d) Paulsen
H (1982) Angew Chem Int Ed Engl 21:155;
(e) Koto S, Morishima N, Zen S (1983) J Synth
Org Chem Jpn 41:701; (f) Paulsen H (1984)
Chem Soc Rev 13:15; (g) Schmidt RR (1986)
Angew Chem Int Ed Engl 25:212; (h) Krohn K
(1987) Nachr Chem Tech Lab 35:930; (i) Kunz
H (1987) Angew Chem Int Ed Engl 26:294;
(j) Schmidt RR (1989) Pure Appl Chem 61:1257;
(k) Hashimoto S, Ikegami S (1991) Farmacia
27:50; (l) Schmidt RR (1991) In: Trost BM
(ed) Comprehensive Organic Synthesis. Pergamon Press, Oxford, vol 6, p 33; (m) Sinaÿ P
(1991) Pure Appl Chem 63:519; (n) Suzuki K,
Nagasawa T (1992) J Synth Org Chem Jpn
50:378; (o) Ito Y, Ogawa T (1992) In: Iguchi Y
(ed) Jikkenkagakukoza. Maruzen, Tokyo, vol
26, p 267; (p) Banoub J (1992) Chem Rev
92:1167; (q) Toshima K, Tatsuta K (1993) Chem
Rev 93:1503; (r) Boons G-J (1996) Tetrahedron
52:1095; (s) Davis BG (2000) J Chem Soc Perkin
Trans 1 2137; (t) Pellissier H (2005) Tetrahedron
61:2947; (u) Fügedi P (2006) In: Levy DE, Fügedi P (eds) The Organic Chemistry of Sugars. CRC
Press, Boca Raton, Fl, p 89
3.1
447
⊡ Scheme 38
Following the extensive studies using a heterogeneous and reusable solid catalyst in a glycosylation reaction by Toshima et al. for greening the chemical glycosylation method [74], the
use of an ionic liquid as an environmentally benign reaction media for the glycosylation of
glycosyl fluoride was reported by Toshima et al. [81]. In this study, it was demonstrated not
only the reusability of the ionic liquid in the glycosylation reaction but also the potency of the
ionic liquid for stereocontrol of the glycosylation reaction ( > Scheme 38).
References
1. Koenigs W, Knorr E (1901) Chem Ber 34:957
2. Lemieux RU, Hayami JI (1965) Can J Chem
43:2162
3. (a) Paulsen H, Lockhoff O (1981) Chem Ber
114:3102; (b) Paulsen H, Kutschker W, Lockhoff
O (1981) Chem Ber 114:3233
4. (a) Wulff G, Röhle G (1974) Angew Chem
Int Ed Engl 13:157; (b) Bochkov A-F, Zaikov
GE (1979) (eds) Chemistry of the O-Glycosidic
Bond: Formation and Cleavage. Pergamon Press,
Oxford; (c) Tsutsumi H, Ishido Y (1980)
J Synth Org Chem Jpn 38:473; (d) Paulsen
H (1982) Angew Chem Int Ed Engl 21:155;
(e) Koto S, Morishima N, Zen S (1983) J Synth
Org Chem Jpn 41:701; (f) Paulsen H (1984)
Chem Soc Rev 13:15; (g) Schmidt RR (1986)
Angew Chem Int Ed Engl 25:212; (h) Krohn K
(1987) Nachr Chem Tech Lab 35:930; (i) Kunz
H (1987) Angew Chem Int Ed Engl 26:294;
(j) Schmidt RR (1989) Pure Appl Chem 61:1257;
(k) Hashimoto S, Ikegami S (1991) Farmacia
27:50; (l) Schmidt RR (1991) In: Trost BM
(ed) Comprehensive Organic Synthesis. Pergamon Press, Oxford, vol 6, p 33; (m) Sinaÿ P
(1991) Pure Appl Chem 63:519; (n) Suzuki K,
Nagasawa T (1992) J Synth Org Chem Jpn
50:378; (o) Ito Y, Ogawa T (1992) In: Iguchi Y
(ed) Jikkenkagakukoza. Maruzen, Tokyo, vol
26, p 267; (p) Banoub J (1992) Chem Rev
92:1167; (q) Toshima K, Tatsuta K (1993) Chem
Rev 93:1503; (r) Boons G-J (1996) Tetrahedron
52:1095; (s) Davis BG (2000) J Chem Soc Perkin
Trans 1 2137; (t) Pellissier H (2005) Tetrahedron
61:2947; (u) Fügedi P (2006) In: Levy DE, Fügedi P (eds) The Organic Chemistry of Sugars. CRC
Press, Boca Raton, Fl, p 89