Solvent-Free Per-O-acetylation of Carbohydrates

Li Cai; Chris Rufty; Megan Liquois

doi:10.14233/ajchem.2014.16573

Issue

Vol. 26 No. 14 (2014): Vol 26 Issue 14

Issue Published : July 5, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Solvent-Free Per-O-acetylation of Carbohydrates

https://doi.org/10.14233/ajchem.2014.16573

Li Cai

Division of Mathematics and Science, University of South Carolina Salkehatchie, 807 Hampton St. Walterboro, SC 29488, USA

Chris Rufty

Department of Chemistry and Biochemistry, University of South Carolina, Columbia, SC 29208, USA

Megan Liquois

Department of Chemical Engineering, University of South Carolina, Columbia, SC 29208, USA

Corresponding Author(s) : Li Cai

caili@mailbox.sc.edu

Asian Journal of Chemistry, Vol. 26 No. 14 (2014): Vol 26 Issue 14
Article Published : July 6, 2014

Abstract

A facile, solvent-free acetylation method promoted by commercial 4Å molecular sieves is described here for the synthesis of per-O-acetylated carbohydrates, which are important intermediates in carbohydrate chemistry. Several examples of carbohydrate and noncarbohydrate substrates are provided.

Keywords

Green chemistry Acylation Carbohydrates Molecular sieves

Cai, L., Rufty, C., & Liquois, M. (2014). Solvent-Free Per-O-acetylation of Carbohydrates. Asian Journal of Chemistry, 26(14), 4367–4369. https://doi.org/10.14233/ajchem.2014.16573

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References

W. Chen, L. Gu, W. Zhang, E. Motari, L. Cai, T.J. Styslinger and P.G. Wang, ACS Chem. Biol., 6, 185 (2011); doi:10.1021/cb100318z.
J.-A.K. Twibanire, R.P. Omran and T.B. Grindley, Org. Lett., 14, 3909 (2012); doi:10.1021/ol301697c.
X. Lu, M.N. Kamat, L. Huang and X. Huang, J. Org. Chem., 74, 7608 (2009); doi:10.1021/jo9016925.
J. Gervay, T.N. Nguyen and M.J. Hadd, Carbohydr. Res., 300, 119 (1997); doi:10.1016/S0008-6215(96)00321-7.
R.R. Kale, C.M. McGannon, C. Fuller-Schaefer, D.M. Hatch, M.J. Flagler, S.D. Gamage, A.A. Weiss and S.S. Iyer, Angew. Chem. Int. Ed., 47, 1265 (2008); doi:10.1002/anie.200703680.
H.C. Hang, C. Yu, D.L. Kato and C.R. Bertozzi, Proc. Natl. Acad. Sci. USA, 100, 14846 (2003); doi:10.1073/pnas.2335201100.
D.J. Vocadlo, H.C. Hang, E.J. Kim, J.A. Hanover and C.R. Bertozzi, Proc. Natl. Acad. Sci. USA, 100, 9116 (2003); doi:10.1073/pnas.1632821100.
X. Duan, L. Cai, L.A. Lee, H. Chen and Q. Wang, Sci. China: Chem., 56, 279 (2013); doi:10.1007/s11426-012-4806-4.
R. Xie, S. Hong, L. Feng, J. Rong and X. Chen, J. Am. Chem. Soc., 134, 9914 (2012); doi:10.1021/ja303853y.
R. Ch, M. Tyagi, P.R. Patil and K.P. Ravindranathan Kartha, Tetrahedron Lett., 52, 5841 (2011); doi:10.1016/j.tetlet.2011.08.141.
D. Mukherjee, B. Ali Shah, P. Gupta and S.C. Taneja, J. Org. Chem., 72, 8965 (2007); doi:10.1021/jo070363i.
W. Wang, W. Cheng, L. Shao and J. Yang, Catal. Lett., 121, 77 (2008); doi:10.1007/s10562-007-9295-2.
N. Ahmed and J.E. van Lier, Tetrahedron Lett., 47, 5345 (2006); doi:10.1016/j.tetlet.2006.05.122.
P.M. Bhaskar and D. Loganathan, Synlett, 129 (1999); doi:10.1055/s-1999-2547.
M.M. Sá and Meier, Synlett, 3474 (2006); doi:10.1055/s-2006-958430.
M. Adinolfi, G. Barone, A. Iadonisi and M. Schiattarella, Tetrahedron Lett., 44, 4661 (2003); doi:10.1016/S0040-4039(03)01072-4.
K.P. Ravindranathan Kartha, B. Mukhopadhyay and R.A. Field, Carbohydr. Res., 339, 729 (2004); doi:10.1016/j.carres.2003.11.021.
M. Mizuno, K. Kobayashi, H. Nakajima, M. Koya and T. Inazu, Synth. Commun., 32, 1665 (2002); doi:10.1081/SCC-120004262.
M. Wallau and U. Schuchardt, J. Braz. Chem. Soc., 6, 393 (1995); doi:10.5935/0103-5053.19950068.
L. Martins and D. Cardoso, Quim. Nova, 29, 358 (2006); doi:10.1590/S0100-40422006000200028.
Yields are isolated yields after chromatography or recrystallization. However, in practice, a simple aqueous work-up is sufficient to afford essentially pure product for subsequent reactions (e.g. preparation of other glycosyl donors or glycosylation).
L. Cai and C. Rufty, Chem. Educ., 18, 96 (2013); doi:10.1007/s00897132480a.
L. Cai, W. Guan, W. Wang, W. Zhao, M. Kitaoka, J. Shen, C. O'Neil and P.G. Wang, Bioorg. Med. Chem. Lett., 19, 5433 (2009); doi:10.1016/j.bmcl.2009.07.104.

References

W. Chen, L. Gu, W. Zhang, E. Motari, L. Cai, T.J. Styslinger and P.G. Wang, ACS Chem. Biol., 6, 185 (2011); doi:10.1021/cb100318z.

J.-A.K. Twibanire, R.P. Omran and T.B. Grindley, Org. Lett., 14, 3909 (2012); doi:10.1021/ol301697c.

X. Lu, M.N. Kamat, L. Huang and X. Huang, J. Org. Chem., 74, 7608 (2009); doi:10.1021/jo9016925.

J. Gervay, T.N. Nguyen and M.J. Hadd, Carbohydr. Res., 300, 119 (1997); doi:10.1016/S0008-6215(96)00321-7.

R.R. Kale, C.M. McGannon, C. Fuller-Schaefer, D.M. Hatch, M.J. Flagler, S.D. Gamage, A.A. Weiss and S.S. Iyer, Angew. Chem. Int. Ed., 47, 1265 (2008); doi:10.1002/anie.200703680.

H.C. Hang, C. Yu, D.L. Kato and C.R. Bertozzi, Proc. Natl. Acad. Sci. USA, 100, 14846 (2003); doi:10.1073/pnas.2335201100.

D.J. Vocadlo, H.C. Hang, E.J. Kim, J.A. Hanover and C.R. Bertozzi, Proc. Natl. Acad. Sci. USA, 100, 9116 (2003); doi:10.1073/pnas.1632821100.

X. Duan, L. Cai, L.A. Lee, H. Chen and Q. Wang, Sci. China: Chem., 56, 279 (2013); doi:10.1007/s11426-012-4806-4.

R. Xie, S. Hong, L. Feng, J. Rong and X. Chen, J. Am. Chem. Soc., 134, 9914 (2012); doi:10.1021/ja303853y.

R. Ch, M. Tyagi, P.R. Patil and K.P. Ravindranathan Kartha, Tetrahedron Lett., 52, 5841 (2011); doi:10.1016/j.tetlet.2011.08.141.

D. Mukherjee, B. Ali Shah, P. Gupta and S.C. Taneja, J. Org. Chem., 72, 8965 (2007); doi:10.1021/jo070363i.

W. Wang, W. Cheng, L. Shao and J. Yang, Catal. Lett., 121, 77 (2008); doi:10.1007/s10562-007-9295-2.

N. Ahmed and J.E. van Lier, Tetrahedron Lett., 47, 5345 (2006); doi:10.1016/j.tetlet.2006.05.122.

P.M. Bhaskar and D. Loganathan, Synlett, 129 (1999); doi:10.1055/s-1999-2547.

M.M. Sá and Meier, Synlett, 3474 (2006); doi:10.1055/s-2006-958430.

M. Adinolfi, G. Barone, A. Iadonisi and M. Schiattarella, Tetrahedron Lett., 44, 4661 (2003); doi:10.1016/S0040-4039(03)01072-4.

K.P. Ravindranathan Kartha, B. Mukhopadhyay and R.A. Field, Carbohydr. Res., 339, 729 (2004); doi:10.1016/j.carres.2003.11.021.

M. Mizuno, K. Kobayashi, H. Nakajima, M. Koya and T. Inazu, Synth. Commun., 32, 1665 (2002); doi:10.1081/SCC-120004262.

M. Wallau and U. Schuchardt, J. Braz. Chem. Soc., 6, 393 (1995); doi:10.5935/0103-5053.19950068.

L. Martins and D. Cardoso, Quim. Nova, 29, 358 (2006); doi:10.1590/S0100-40422006000200028.

Yields are isolated yields after chromatography or recrystallization. However, in practice, a simple aqueous work-up is sufficient to afford essentially pure product for subsequent reactions (e.g. preparation of other glycosyl donors or glycosylation).

L. Cai and C. Rufty, Chem. Educ., 18, 96 (2013); doi:10.1007/s00897132480a.

L. Cai, W. Guan, W. Wang, W. Zhao, M. Kitaoka, J. Shen, C. O'Neil and P.G. Wang, Bioorg. Med. Chem. Lett., 19, 5433 (2009); doi:10.1016/j.bmcl.2009.07.104.

Issue

Vol. 26 No. 14 (2014): Vol 26 Issue 14

Solvent-Free Per-O-acetylation of Carbohydrates

Corresponding Author(s) : Li Cai

Abstract

Keywords

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