Synthesis 2021; 53(11): 2000-2006
DOI: 10.1055/s-0040-1705990
paper

Development of a Novel Method for Trimethylsilylation of Saccharides­

Jyun-Siao Chen
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Yi-Fan Ke
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Heng-Yan Lin
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Wesley Lin
b   Morrison Academy, Taichung 406, Taiwan
,
Wei-Chung Yen
c   Taipei Municipal Neihu High School, Taipei 114, Taiwan
,
Hsin-Ru Wu
d   Instrumentation Center, MOST, National Tsing Hua University, Hsinchu 300, Taiwan
,
Shun-Yuan Luo
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
› Author Affiliations
The authors thank the Ministry of Science and Technology (MOST) in Taiwan (MOST 107-2113-M-005-021) and National Chung Hsing University for financial support.


Abstract

The trimethylsilyl (TMS) group is widely used in carbo­hydrate synthesis, although this protecting group is unstable and its post-synthetic purification challenging. The successful trimethylsilyl­ation of carbohydrates mediated by recyclable and efficient acidic catalyst PTA/HMDS and the novel reagent, TMSOAc (TEA/TMSOAc), under alkaline condition is reported. The advantages of these methods are that the reactions proceed in good to excellent yields without applying column chromatography for purification.

Supporting Information



Publication History

Received: 18 October 2020

Accepted after revision: 10 November 2020

Article published online:
19 January 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

    • 1a Hudak JE, Bertozzi CR. Chem. Biol. 2014; 21: 16
    • 1b Kiessling LL, Splain RA. Annu. Rev. Biochem. 2010; 79: 619
    • 1c Chung K, Waymouth RM. ACS Catal. 2016; 6: 4653
    • 2a Van Kooyk Y, Rabinovich GA. Nat. Immunol. 2008; 9: 593
    • 2b Cummings RD. Mol. BioSyst. 2009; 5: 1087
    • 2c Galan MC, Benito-Alifonso D, Watt GM. Org. Biomol. Chem. 2011; 9: 3598
    • 2d Shie C.-R, Tzeng Z.-H, Wang C.-C, Hung S.-C. J. Chin. Chem. Soc. 2009; 56: 510
  • 3 Jäger M, Minnaard AJ. Chem. Commun. 2016; 52: 656
    • 4a Liu Q, Janssen MH. A, Van Rantwijk F, Sheldon RA. Green Chem. 2005; 7: 39
    • 4b Carrero-Carralero C, Ruiz-Aceituno L, Ramos L, Moreno FJ, Sanz ML. Ind. Eng. Chem. Res. 2014; 53: 13843
    • 4c Joseph AA, Verma VP, Liu X.-Y, Wu C.-H, Dhurandhare VM, Wang C.-C. Eur. J. Org. Chem. 2012; 4: 744
  • 5 Pramanik S, Fernandes A, Liautard V, Pucheault M, Robert F, Landais Y. Chem. Eur. J. 2019; 25: 728
    • 6a Jia J, Zeng X, Liu Z, Zhao L, He C.-Y, Li X.-F, Feng Z. Org. Lett. 2020; 22: 2816
    • 6b Pu X, Hu J, Zhao Y, Shi Z. ACS Catal. 2016; 6: 6692
  • 7 Takahashi T, Ogasawara S, Shinozaki Y, Tamiaki H. Eur. J. Org. Chem. 2019; 6383
    • 8a Corey EJ, Snider BB. J. Am. Chem. Soc. 1972; 94: 2549
    • 8b Hart TW, Metcalfe DA, Scheinmann F. J. Chem. Soc., Chem. Commun. 1979; 156
    • 8c Corey EJ, Venkateswarlu A. J. Am. Chem. Soc. 1972; 94: 6190
    • 9a Zhang ZH, Li TS, Yang F, Fu CG. Synth. Commun. 1998; 28: 3105
    • 9b Kadam ST, Kim SS. Green Chem. 2010; 12: 94
    • 10a Gevorgyan V, Rubin M, Benson S, Liu J.-X, Yamamoto Y. J. Org. Chem. 2000; 65: 6179
    • 10b Horner L, Mathias J. J. Organomet. Chem. 1985; 282: 175
    • 10c Keiji Y, Makoto T. Bull. Chem. Soc. Jpn. 1989; 62: 2111
  • 11 Fukumoto Y, Hirano M, Chatani N. ACS Catal. 2017; 7: 3152
    • 12a Yoshikawa M, Tamura Y, Wakabayashi R, Tamai M, Shimojima A, Kuroda K. Angew. Chem. Int. Ed. 2017; 56: 13990
    • 12b Wang CC, Lee JC, Luo SY, Kulkarni SS, Huang YW, Lee CC, Chang KL, Hung SC. Nature 2007; 446: 896
    • 12c Chang K.-L, Zulueta MM. L, Lu X.-A, Zhong Y.-Q, Hung S.-C. J. Org. Chem. 2010; 75: 7424
    • 12d Huang T.-Y, Zulueta MM. L, Hung S.-C. Org. Lett. 2011; 13: 1506
    • 12e Patil PS, Lee C.-C, Huang Y.-W, Zulueta MM. L, Hung S.-C. Org. Biomol. Chem. 2013; 11: 2605
    • 12f Huang Y.-W, Zulueta MM. L, Hung S.-C. Org. Biomol. Chem. 2014; 12: 376
    • 12g Chen CW, Wang CC, Li XR, Witek H, Mong K.-KT. Org. Biomol. Chem. 2020; 18: 3135
    • 13a Seddighi M, Shirini F, Goli-Jolodar O. RSC Adv. 2016; 6: 23564
    • 13b Nikbakht F, Ghonchepour E, Ziyadi H, Heydari A. RSC Adv. 2014; 4: 34428
    • 13c Moghadam M, Tangestaninejad S, Mirkhani V, Mohammadpoor Baltork I, Gharaati S. Appl. Organomet. Chem. 2009; 23: 446
    • 14a Gauttret P, El-Ghamarti S, Legrand A, Coutrier D, Rigo B. Synth. Commun. 1996; 26: 707
    • 14b Shirini F, Mollarazi E. Catal. Commun. 2007; 8: 1393
    • 14c Firouzabadi H, Iranpoor N, Amani K, Nowrouzi F. J. Chem. Soc., Perkin Trans. 1 2002; 2601
    • 14d Karimi B, Golshani B. J. Org. Chem. 2000; 65: 7228
    • 14e Yadav JS, Reddy BV. S, Basak AK, Baishya G, Venkat Narsaiah A. Synthesis 2006; 3831
    • 14f Akhlaghinia B, Tavakoli S. Synthesis 2005; 1775
    • 14g Zareyeea D, Karimi B. Tetrahedron Lett. 2007; 48: 1277
    • 14h Mojtahedi MM, Abbasi H, Abaee MS. J. Mol. Catal. A: Chem. 2006; 250: 6
    • 14i Ghorbani-Vaghei R, Zolfigol MA, Chegeny M, Veisi H. Tetrahedron Lett. 2006; 47: 4505
    • 14j Firouzabadi H, Iranpoor N, Jafari AA, Jafari MR. J. Organomet. Chem. 2008; 693: 2711
    • 14k Mojtahedi MM, Abaee MS, Eghtedari M. Appl. Organomet. Chem. 2008; 22: 529
    • 14l Shirini F, Abedini M. J. Iran. Chem. Soc. 2008; 5: S87
    • 14m Khazaei A, Zolfigol MA, Rostami A, Choghamarani AG. Catal. Commun. 2007; 8: 543
    • 14n Shaterian HR, Shahrekipoor F, Ghashang M. J. Mol. Catal. A: Chem. 2007; 272: 142
    • 14o Shirakawa E, Hironaka K, Otsuka H, Hayashi T. Chem. Commun. 2006; 3927
  • 15 Chen J.-S, Sankar A, Lin Y.-J, Huang P.-H, Liao C.-H, Wu S.-S, Wu H.-R, Luo S.-Y. RSC Adv. 2019; 9: 33853
  • 16 Shi W, Zhao J, Yuan X, Wang S, Wang X, Huo M. Chem. Eng. Technol. 2012; 35: 347
  • 17 Wang G.-W, Shen Y.-B, Wu X.-L. Eur. J. Org. Chem. 2008; 4367
  • 18 Shtelman AV, Becker JY. Tetrahedron 2011; 67: 1135
  • 19 Qin L, Hu B, Neumann KD, Linstad EJ, McCauley K, Veness J, Kempinger JJ, DiMagno SG. Eur J. Org. Chem. 2015; 27: 5919