Issue

Vol. 37 No. 11 (2025): Vol 37 Issue 11, 2025

Copyright (c) 2025 Gan Bajracharya, Sanju Maharjan, Nawaraj Karki, Ganga Ram Upadhayay, Sabita Shrestha, Binjita Pandey, Amrita Neupane, Ankita Belbase

Creative Commons License

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

Anomeric Distribution of Sugar Acetates Synthesized via Peracetylation of Monosaccharides under Acidic and Basic Conditions

https://doi.org/10.14233/ajchem.2025.34481
Gan B. Bajracharya
Catalysis and Frontier Molecules Synthesis Laboratory, Faculty of Science, Nepal Academy of Science and Technology, Khumaltar, Lalitpur, Nepal
https://orcid.org/0000-0002-3061-6557
Sanju Maharjan
Catalysis and Frontier Molecules Synthesis Laboratory, Faculty of Science, Nepal Academy of Science and Technology, Khumaltar, Lalitpur, Nepal
https://orcid.org/0009-0006-2956-9462
Nawaraj Karki
Catalysis and Frontier Molecules Synthesis Laboratory, Faculty of Science, Nepal Academy of Science and Technology, Khumaltar, Lalitpur, Nepal
https://orcid.org/0009-0004-2999-7796
Ganga Ram Upadhayay
Catalysis and Frontier Molecules Synthesis Laboratory, Faculty of Science, Nepal Academy of Science and Technology, Khumaltar, Lalitpur, Nepal
https://orcid.org/0009-0007-6641-423X
Sabita Shrestha
Catalysis and Frontier Molecules Synthesis Laboratory, Faculty of Science, Nepal Academy of Science and Technology, Khumaltar, Lalitpur, Nepal
https://orcid.org/0009-0005-5947-108X
Binjita Pandey
Catalysis and Frontier Molecules Synthesis Laboratory, Faculty of Science, Nepal Academy of Science and Technology, Khumaltar, Lalitpur, Nepal
https://orcid.org/0009-0004-8142-9083
Amrita Neupane
Catalysis and Frontier Molecules Synthesis Laboratory, Faculty of Science, Nepal Academy of Science and Technology, Khumaltar, Lalitpur, Nepal; Department of Chemistry, Tri-Chandra Multiple Campus, Tribhuvan University, Ghantaghar, Kathmandu, Nepal
https://orcid.org/0009-0002-6361-2947
Ankita Belbase
Catalysis and Frontier Molecules Synthesis Laboratory, Faculty of Science, Nepal Academy of Science and Technology, Khumaltar, Lalitpur, Nepal; Department of Chemistry, Tri-Chandra Multiple Campus, Tribhuvan University, Ghantaghar, Kathmandu, Nepal

Corresponding Author(s) : Gan B. Bajracharya

ganbajracharya@yahoo.com

Asian Journal of Chemistry, Vol. 37 No. 11 (2025): Vol 37 Issue 11, 2025

Abstract

Peracetylation of D-glucose (1a), D-galactose (1b), D-mannose (1c), D-fructose (1d) and L-arabinose (1e) with stoichiometric amount of acetic anhydride was performed in the presence of either 1.7 mol% HClO4 or 30 mol% NaOAc as catalyst to yield corresponding sugar acetates (2a-e). Upon direct column chromatography of the crude reaction mixtures, the products were obtained in good to excellent yield (up to 96.1%). Composition of α-pyranose, β-pyranose, α-furanose, β-furanose and open-chain anomers present in the sugar acetates (2a-e) was determined by 1H NMR. Pyranose was the major anomer produced in all the cases except, the NaOAc-catalyzed peracetylation of a ketohexose (1d) exclusively produced furanose.

Keywords

Carbohydrate Catalysis Glycoside Perchloric acid Sodium acetate Synthesis
(1)
Bajracharya, G. B.; Maharjan, S.; Karki, N.; Upadhayay, G. R.; Shrestha, S.; Pandey, B.; Neupane, A.; Belbase, A. Anomeric Distribution of Sugar Acetates Synthesized via Peracetylation of Monosaccharides under Acidic and Basic Conditions. ajc 2025, 37, 2766-2772.
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. P. Wlodarczyk, M. Paluch, A. Wlodarczykc and M. Hyra, Phys. Chem. Chem. Phys., 16, 4694 (2014); https://doi.org/10.1039/C3CP54833C
  2. S. Ha, J. Gao, B. Tidor, J.W. Brady and M. Karplus, J. Am. Chem. Soc., 113, 1553 (1991); https://doi.org/10.1021/ja00005a015
  3. G. Huang, Q. Tang, D. Li, Y. Huang and D. Zhang, Curr. Org. Synth., 13, 82 (2016); https://doi.org/10.2174/1570179412999150703112245
  4. P.J. Garegg, Acc. Chem. Res., 25, 575 (1992); https://doi.org/10.1021/ar00024a005
  5. K. Toshima and K. Tatsuta, Chem. Rev., 93, 1503 (1993); https://doi.org/10.1021/cr00020a006
  6. R.A. Dwek, Chem. Rev., 96, 683 (1996); https://doi.org/10.1021/cr940283b
  7. K.C. Nicolaou and H.J. Mitchell, Angew. Chem. Int. Ed., 40, 1576 (2001); https://doi.org/10.1002/1521-3773(20010504)40:9<1576::AID-ANIE15760>3.0.CO; 2-G
  8. B.G. Davis, Chem. Rev., 102, 579 (2002); https://doi.org/10.1021/cr0004310
  9. C.S. Hudson and J.K. Dale, J. Am. Chem. Soc., 37, 1264 (1915); https://doi.org/10.1021/ja02170a025
  10. G. Höfle, W. Steglich and H. Vorbrüggen, Angew. Chem. Int. Ed. Engl., 17, 569 (1978); https://doi.org/10.1002/anie.197805691
  11. R.B. Cohen, K.-C. Tsou, S.H. Rutenburg and A.M. Seligman, J. Biol. Chem., 195, 239 (1952); https://doi.org/10.1016/S0021-9258(19)50894-8
  12. R.U. Lemieux, R.K. Kullnig, H.J. Bernstein and W.G. Schneider, J. Am. Chem. Soc., 80, 6098 (1958); https://doi.org/10.1021/ja01555a051
  13. R. Ch, M. Tyagi, P.R. Patil and K.P.R. Kartha, Tetrahedron Lett., 52, 5841 (2011); https://doi.org/10.1016/j.tetlet.2011.08.141
  14. J. A. Hyatt and G. William Tindall, Heterocycles, 35, 227 (1993); https://doi.org/10.3987/COM-92-S8
  15. H. Binch, K. Stangier and J. Thiem, Carbohydr. Res., 306, 409 (1998); https://doi.org/10.1016/S0008-6215(97)10094-5
  16. C. Limousin, J. Cléophax, A. Petit, A. Loupy and G. Lukacs, J. Carbohydr. Chem., 16, 327 (1997); https://doi.org/10.1080/07328309708006533
  17. F. Dasgupta, P.P. Singh and H.C. Srivastava, Carbohydr. Res., 80, 346 (1980); https://doi.org/10.1016/S0008-6215(00)84876-4
  18. J.-C. Lee, C.-A. Tai and S.-C. Hung, Tetrahedron Lett., 43, 851 (2002); https://doi.org/10.1016/S0040-4039(01)02253-5
  19. C.-A. Tai, S.S. Kulkarni and S.-C. Hung, J. Org. Chem., 68, 8719 (2003); https://doi.org/10.1021/jo030073b
  20. K.K. Chauhan, C.G. Frost, I. Love and D. Waite, Synlett, 1999, 1743 (1999); https://doi.org/10.1055/s-1999-2941
  21. A. Orita, C. Tanahashi, A. Kakuda and J. Otera, Angew. Chem. Int. Ed., 39, 2877 (2000); https://doi.org/10.1002/1521-3773(20000818)39:16<2877::AID-ANIE2877>3.0.CO; 2-V
  22. G. Bartoli, R. Dalpozzo, A. De Nino, L. Maiuolo, M. Nardi, A. Procopio and A. Tagarelli, Green Chem., 6, 191 (2004); https://doi.org/10.1039/b400920g
  23. C.-T. Chen, J.-H. Kuo, C.-H. Li, N.B. Barhate, S.-W. Hon, T.-W. Li, S.-D. Chao, C.-C. Liu, Y.-C. Li, I.-H. Chang, J.-S. Lin, C.-J. Liu and Y.-C. Chou, Org. Lett., 3, 3729 (2001); https://doi.org/10.1021/ol016684c
  24. J.Ø. Duus, C.H. Gotfredsen and K. Bock, Chem. Rev., 100, 4589 (2000); https://doi.org/10.1021/cr990302n
  25. G.B. Bajracharya and S.S. Shrestha, Synth. Commun., 48, 1688 (2018); https://doi.org/10.1080/00397911.2018.1459721
  26. N. Bajracharya, S. Shrestha and G.B. Bajracharya, Asian J. Chem., 36, 859 (2024); https://doi.org/10.14233/ajchem.2024.31196
  27. M.U. Roslund, P. Tähtinen, M. Niemitz and R. Sjöholm, Carbohydr. Res., 343, 101 (2008); https://doi.org/10.1016/j.carres.2007.10.008
  28. J. Zhang, B. Zhang, J. Zhou, J. Li, C. Shi, T. Huang, Z. Wang and J. Tang, J. Carbohydr. Chem., 30, 165 (2011); https://doi.org/10.1080/07328303.2011.621042
  29. R.U. Lemieux and J.D. Stevens, Can. J. Chem., 43, 2059 (1965); https://doi.org/10.1139/v65-276
  30. J.D. Stevens, Carbohydr. Res., 347, 9 (2012); https://doi.org/10.1016/j.carres.2011.09.009
  31. Y. Zhu, J. Zajicek and A.S. Serianni, J. Org. Chem., 66, 6244 (2001); https://doi.org/10.1021/jo010541m
  32. T. Barclay, M. Ginic-Markovic, M.R. Johnston, P. Cooper and N. Petrovsky, Carbohydr. Res., 347, 136 (2012); https://doi.org/10.1016/j.carres.2011.11.003
  33. F. Franks, Pure Appl. Chem., 59, 1189 (1987); https://doi.org/10.1351/pac198759091189
  34. S.T. Summerfelt, E.J.-M. Selosse, P.J. Reilly and W.S. Trahanovsky, Carbohydr. Res., 203, 163 (1990); https://doi.org/10.1016/0008-6215(90)80014-T
  35. D. Horton and P.L. Durette, J. Org. Chem., 36, 2658 (1971); https://doi.org/10.1021/jo00817a019
Read More
Author biographies is not available.
Crossref
Scopus
Google Scholar
Europe PMC
Download
PDF
Statistic
Read Counter : 263 Download : 114
PlumX