PDF herunterladen
Synthesis 2022; 54(12): 2825-2838
DOI: 10.1055/a-1751-1225
paper

4-(tert-Butyldiphenylsilyloxy)-2,2-dimethylbutanoyl: An Easily Removable Pivaloyl-Type Protecting Group with High Orthogonality

Qishuai Li
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Yong Su
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Zhi Qiao
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Jianjun Wang
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Peng Wang
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Sumei Ren
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
b   Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, P. R. of China
,
Ni Song
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
b   Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, P. R. of China
,
Ming Li  ∗
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
b   Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, P. R. of China
› InstitutsangabenWe are grateful for financial support from the National Natural Science Foundation of China (Grant No. 21977088), the National Natural Science Foundation of China-Shandong Joint Foundation (Grant No. U1906213), and the Natural Science Foundation of Shandong Province (Grant No. ZR2018MB015).
› Weitere Informationen
    Lizenzen und Reprints Alle Artikel dieser Rubrik


Abstract

Protecting groups play multiple and vital roles during the synthesis of carbohydrates and other natural products. We herein report the installation and orthogonal cleavage, under mild conditions, of a 4-(tert-butyldiphenylsilyloxy)-2,2-dimethylbutanoyl (BDMB) group as a sterically hindered pivaloyl-type hydroxy protecting group. The compatibility of this substituent with the removal of other protecting groups is also investigated. Due to its advantageous properties, BDMB is anticipated to function as a valuable agent for masking hydroxy groups.

Keywords

4-(tert-butyldiphenylsilyloxy)-2,2-dimethylbutanoyl - carbohydrates - protecting groups - assisted cleavage - tetrabutylammonium fluoride - acetic acid

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1751-1225.
  • Supporting Information


Publikationsverlauf

Eingereicht: 11. Januar 2022

Angenommen nach Revision: 26. Januar 2022

Accepted Manuscript online:
26. Januar 2022

Artikel online veröffentlicht:
23. März 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Schelhaas M, Waldmann H. Angew. Chem. Int. Ed. 1996; 35: 2056
      Crossref
    • 1b Greene TW, Wuts PG. M. Protective Groups in Organic Synthesis, 5th ed. John Wiley & Sons; Hoboken: 2014
      Google Scholar
    • 2a Codée JD. C, Overkleeft HS, Ali A, van der Marel GA. C. R. Chim. 2011; 14: 178
      Crossref
    • 2b Wang T, Demchenko AV. Org. Biomol. Chem. 2019; 17: 4934
      CrossrefPubMed
    • 2c Vidal S. Angew. Chem. Int. Ed. 2019; 58: 13628
      CrossrefPubMed
    • 2d Ghosh B, Kulkarni SS. Chem. Asian J. 2020; 15: 450
      CrossrefPubMed
    • 3a Zeng Y, Wang Z, Whitfield D, Huang X. J. Org. Chem. 2008; 73: 7952
      CrossrefPubMed
    • 3b Guo J, Ye X.-S. Molecules 2010; 15: 7235
      CrossrefPubMed
    • 3c van der Vorm S, Hansen T, van Hengst JM. A, Overkleeft HS, van der Marel GA, Codée JD. C. Chem. Soc. Rev. 2019; 48: 4688
      CrossrefPubMed
    • 3d Chang C, Lin M, Chan C, Su K, Wu C, Lo W, Lam S, Cheng Y, Liao P, Wong C, Wang C. Angew. Chem. Int. Ed. 2021; 60: 12413
      CrossrefPubMed
    • 4a Kunz H, Harreus A. Liebigs Ann. Chem. 1982; 41
      Crossref
    • 4b Harreus A, Kunz H. Liebigs Ann. Chem. 1986; 717
      Crossref
    • 4c Sato S, Nunomura S, Nakano T, Ito Y, Ogawa T. Tetrahedron Lett. 1988; 29: 4097
      Crossref
    • 4d Scott IL, Market RV, DeOrazio RJ, Meckler H, Kogan TP. Carbohydr. Res. 1999; 317: 210
      Crossref
    • 6a Nicolaou KC, Caulfield TJ, Kataoka H, Stylianides NA. J. Am. Chem. Soc. 1990; 112: 3693
      Crossref
    • 6b Mori K, Qian Z.-H. Bull. Soc. Chim. Fr. 1993; 130: 382
  • 7 Crimmins MT, Carroll CA, Wells AJ. Tetrahedron Lett. 1998; 39: 7005
    Crossref
    • 8a Trost BM, Hembre EJ. Tetrahedron Lett. 1999; 40: 219
      Crossref
    • 8b Haley HM. S, Hill AG, Greenwood AI, Woerly EM, Rienstra CM, Burke MD. J. Am. Chem. Soc. 2018; 140: 15227
      CrossrefPubMed
  • 9 Castelli R, Overkleeft HS, van der Marel GA, Codée JD. C. Org. Lett. 2013; 15: 2270
    CrossrefPubMed
    • 10a Volbeda AG, Reintjens NR. M, Overkleeft HS, van der Marel GA, Codée JD. C. Eur. J. Org. Chem. 2016; 31: 5282
      Crossref
    • 10b Volbeda AG, van Mechelen J, Meeuwenoord N, Overkleeft HS, van der Marel GA, Codée JD. C. J. Org. Chem. 2017; 82: 12992
      CrossrefPubMed
    • 11a Liu H, Zhou S.-Y, Wen G.-N, Liu X.-X, Liu D.-Y, Zhang Q.-J, Schmidt RR, Sun J.-S. Org. Lett. 2019; 21: 8049
      CrossrefPubMed
    • 11b Liu H, Hansen T, Zhou S.-Y, Wen G.-N, Liu X.-X, Zhang Q.-J, Codée JD. C, Schmidt RR, Sun J.-S. Org. Lett. 2019; 21: 8713
      CrossrefPubMed
    • 12a Ágoston K, Streicher H, Fügedi P. Tetrahedron: Asymmetry 2016; 27: 707
      Crossref
    • 12b Weber J, Krauter S, Schwarz T, Hametner C, Mikula H. Synlett 2018; 29: 2265
      Artikel in Thieme Connect
    • 13a van den Bos LJ, Dinkelaar J, Overkleeft HS, van der Marel GA. J. Am. Chem. Soc. 2006; 128: 13066
      CrossrefPubMed
    • 13b Codée JD. C, van den Bos LJ, de Jong A.-R, Dinkelaar J, Lodder G, Overkleeft HS, van der Marel GA. J. Org. Chem. 2009; 74: 38
      CrossrefPubMed
    • 13c Walvoort MT. C, van den Elst H, Plante OJ, Kröck L, Seeberger PH, Overkleeft HS, van der Marel GA, Codée JD. C. Angew. Chem. Int. Ed. 2012; 51: 4393
      CrossrefPubMed
  • 14 Li T, Wang J, Zhu X, Zhou X, Sun S, Wang P, Cao H, Yu G, Li M. J. Am. Chem. Soc. 2021; 143: 11171
    CrossrefPubMed
  • 15 Lee HY, Shin SS, Kim WY. Chem. Asian J. 2012; 7: 2450
    CrossrefPubMed
    • 16a Codée JD. C, de Jong AR, Dinkelaar J, Overkleeft HS, van der Marel GA. Tetrahedron 2009; 65: 3780
      Crossref
    • 16b Lodder G, Overkleeft HS, Codée JD. C, van der Marel GA. J. Org. Chem. 2011; 76: 7301
      CrossrefPubMed
    • 17a Llewellyn JW, Williams JM. Carbohydr. Res. 1972; 22: 221
      Crossref
    • 17b Werschkun B, Thiem J. Synthesis 1999; 121
      Artikel in Thieme Connect
    • 17c Sugawara S, Meguro Y, Sato S, Enomoto M, Ogura Y, Kuwahara S. Tetrahedron Lett. 2020; 61: 151891
      Crossref
    • 18a Ekholm FS, Leino R. Acyl Migrations in Carbohydrate Chemistry: Strategies and Applications in Carbohydrate Chemistry. Vidal S. Wiley-VCH; Weinheim: 2019: 227
      Google Scholar
    • 18b Crich D. Chem. Rev. 2020; 120: 7104
      CrossrefPubMed
    • 18c Govindarajan M. Carbohydr. Res. 2020; 497: 108151
      CrossrefPubMed
  • 19 Kim DW, Jeong HJ, Lim ST, Sohn MH. Angew. Chem. Int. Ed. 2008; 120: 8532
    Crossref
    • 20a Illing HP. A, Wilson ID. Biochem. Pharmacol. 1981; 30: 3381
      CrossrefPubMed
    • 20b Schwarz JB, Kuduk SD, Chen X.-T, Sames D, Glunz PW, Danishefsky SJ. J. Am. Chem. Soc. 1999; 121: 2662
      Crossref
  • 21 Kelly DR, Roberts SM, Newton RF. Synth. Commun. 1979; 9: 295
    Crossref
  • 22 Chen X, Xu P, Xu Y, Liu L, Liu Y, Zhu D, Lei P. Bioorg. Med. Chem. Lett. 2012; 22: 7402
    CrossrefPubMed
  • 23 DeNinno MP, Etienne JB, Duplantier KC. Tetrahedron Lett. 1995; 36: 669
    CrossrefPubMed
  • 24 Yang S, Wang A.-P, Zhang G, Di X, Zhao Z, Lei P. Tetrahedron 2016; 72: 5659
    Crossref
  • 25 Wang C.-C, Lee J.-C, Luo S.-Y, Suvarn SK, Huang Y.-W, Lee C.-C, Chang K.-L, Hung S.-C. Nature 2007; 446: 896
    CrossrefPubMed
  • 26 Li T, Li T, Linseis M, Wang F, Winter RF, Schmidt RR, Peng P. ACS Catal. 2020; 10: 11406
    Crossref
  • 27 Zhang L, Shen K, Taha HA, Lowary TL. J. Org. Chem. 2018; 83: 7659
    CrossrefPubMed
  • 28 Ren B, Cai L, Zhang L, Yang Z, Zhang L. Tetrahedron Lett. 2005; 46: 8083
    Crossref
    • 29a Fujii H, Shimada N, Ohtawa M, Karaki F, Koshizuka M, Hayashida K, Kamimura M, Makino K, Nagamitsu T, Nagase H. Tetrahedron 2017; 73: 5425
      Crossref
    • 29b Ochiai H, Niwa T, Hosoya T. Org. Lett. 2016; 18: 5982
      CrossrefPubMed
  • 30 Zhang L, Li L, Bai S, Zhou X, Wang P, Li M. Org. Lett. 2016; 18: 6030
    CrossrefPubMed
  • 31 Huang JS, Huang W, Meng X, Wang X, Gao PC, Yang JS. Angew. Chem. Int. Ed. 2015; 54: 10894
    CrossrefPubMed
  • 32 van der Vorm S, Hansen T, Overkleeft HS, van der Marel GA, Codée JD. C. Chem. Sci. 2017; 8: 1867
    CrossrefPubMed
  • 33 Chayajarus K, Chambers DJ, Chughtai MJ, Fairbanks AJ. Org. Lett. 2004; 6: 3797
    CrossrefPubMed
  • 34 Werz DB, Seeberger PH. Angew. Chem. Int. Ed. 2005; 44: 6315
    CrossrefPubMed
  • 35 Möker J, Thiem J. Carbohydr. Res. 2012; 348: 14
    CrossrefPubMed