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Regioselectivity of Tin-Mediated Benzylation of Glycoside
Corresponding Author(s) : Xin Lou
Asian Journal of Chemistry,
Vol. 25 No. 4 (2013): Vol 25 Issue 4
Abstract
Regioselectivity of methyl a-D-glucopyranoside benzylation using dibutyltin dimethoxide (DBDM) as stannylating agent was probed, general factors affecting regioselectivity have been examined. The results show the O-2 position of glucoside has advantage of being benzylated over the O-6 position. The major isomers of benzyl ether were separated by preparative HPLC method and characterized.
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- C.B. Reese, in ed.: J.F.W. McOmie, Protective Groups in Organic Chemistry, Plenum Press, London (1973).
- T. Green, Protective Groups in Organic Synthesis, John Wiley & Sons, NY, 29 (1981).
- C.M. McCloskey, Adv. Carbohyd. Chem., 12, 137 (1957).
- R.W. Binkley and H.G. Ambrose, J. Carbohyd. Chem., 3, 1 (1984).
- H. Paulsen, Angew. Chem. Int. Ed., 21, 155 (1982).
- R.R. Schmidt, Angew. Chem. Int. Ed., 25, 212 (1986).
- S. David and S. Hanessian, Tetrahedron, 41, 643 (1985).
- M. Pereyre, J.-P. Quintard and A. Rahm, London: Butterworths, Chap. 11 (1987).
- T.B. Grindley and D.C. Washington, ACS, Chap. 4 (1994).
- S. Hannesian, Preparative Carbohydrate Chemistry. New York: Marcel Dekker Inc., Chap. 4 (1997).
- A.G. Goncalves, M.D. Noseda, M.E.R. Duarte and T.B. Grindly, J. Org. Chem., 72, 9896 (2007).
- X. Lou, J. O'Brien, G. Henehan and S. Cassidy, Asian J. Chem., 22, 3135 (2010).
- M.W. Bredenkamp, C.W. Holzapfel and F.S. Toerian, Afr. J. Chem., 44, 97 (1991).
- C.W. Holzapfel, J.J. Huyser, V.T.L. Merwe and F.R. Heerden,Heterocycles, 32, 1445 (1991).
- M.W.S. Bredenkamp, Afr. J. Chem., 48, 154 (1995).
References
C.B. Reese, in ed.: J.F.W. McOmie, Protective Groups in Organic Chemistry, Plenum Press, London (1973).
T. Green, Protective Groups in Organic Synthesis, John Wiley & Sons, NY, 29 (1981).
C.M. McCloskey, Adv. Carbohyd. Chem., 12, 137 (1957).
R.W. Binkley and H.G. Ambrose, J. Carbohyd. Chem., 3, 1 (1984).
H. Paulsen, Angew. Chem. Int. Ed., 21, 155 (1982).
R.R. Schmidt, Angew. Chem. Int. Ed., 25, 212 (1986).
S. David and S. Hanessian, Tetrahedron, 41, 643 (1985).
M. Pereyre, J.-P. Quintard and A. Rahm, London: Butterworths, Chap. 11 (1987).
T.B. Grindley and D.C. Washington, ACS, Chap. 4 (1994).
S. Hannesian, Preparative Carbohydrate Chemistry. New York: Marcel Dekker Inc., Chap. 4 (1997).
A.G. Goncalves, M.D. Noseda, M.E.R. Duarte and T.B. Grindly, J. Org. Chem., 72, 9896 (2007).
X. Lou, J. O'Brien, G. Henehan and S. Cassidy, Asian J. Chem., 22, 3135 (2010).
M.W. Bredenkamp, C.W. Holzapfel and F.S. Toerian, Afr. J. Chem., 44, 97 (1991).
C.W. Holzapfel, J.J. Huyser, V.T.L. Merwe and F.R. Heerden,Heterocycles, 32, 1445 (1991).
M.W.S. Bredenkamp, Afr. J. Chem., 48, 154 (1995).