Synthesis 2022; 54(03): 754-762
DOI: 10.1055/a-1654-2211
paper

Trimethylsilyl Esters as Novel Dual-Purpose Protecting Reagents

Jyun-Siao Chen
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Po-Hsun Huang
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Ya-Chi Hsieh
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Jen-Wei Liu
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Hsiao-Lin Hsu
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Kai-Min Zhang
a   Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
,
Ren-Tsung Wu
b   Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes, Miaoli 350, Taiwan
,
Ting-Shuo Chang
c   National Chutung Senior High School, Hsinchu 310, Taiwan
,
Yu-Hao Liu
c   National Chutung Senior High School, Hsinchu 310, Taiwan
,
Hsin-Ru Wu
c   National Chutung Senior High School, Hsinchu 310, 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 in Taiwan (MOST 106-2113-M-005-007 and 107-2113-M-005-021 for S.-Y. Luo), National Chung Hsing University, and Chia Nan University of Pharmacy and Science for financial support.


Abstract

Trimethylsilyl esters, AcOTMS, BzOTMS, TCAOTMS, etc., are inexpensive and chemically stable reagents that pose a negligible environmental hazard. Such compounds prove to serve as efficient dual-purpose reagents to respectively achieve acylation and trimethylsilylation of alcohols under acidic or basic conditions. Herein, a detailed study on protection of various substrates and new methodological investigations is described.

Supporting Information



Publication History

Received: 09 August 2021

Accepted after revision: 27 September 2021

Accepted Manuscript online:
27 September 2021

Article published online:
17 November 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

    • 1a Kalla RM. N, Reddy SS, Kim I. Catal. Lett. 2019; 149: 2696
    • 1b Protecting Groups: Strategies and Applications in Carbohydrate Chemistry. Vidal S. Wiley-VCH; Weinheim: 2018. 4th ed
    • 1c Ghosh B, Kulkarni SS. Chem. Asian J. 2020; 15: 450
  • 2 Lugemwa FN, Shaikh K, Hochstedt E. Catalysts 2013; 3: 954
    • 3a Evans DA, Tanis SP, Hart DJ. J. Am. Chem. Soc. 1981; 103: 5813
    • 3b Enders D, Geibel G, Osborne S. Chem. Eur. J. 2000; 6: 1302
    • 3c Jarowicki K, Kocienski P. J. Chem. Soc., Perkin Trans. 1 1999; 1589
    • 3d Smith MB. Organic Synthesis, 4th ed.. Academic Press; New York: 2017: 185
    • 4a Jin TS, Ma YR, Zhang ZH, Li TS. Synth. Commun. 1998; 28: 3173
    • 4b Iranpoor N, Shekarriz M. Bull. Chem. Soc. Jpn. 1999; 72: 455
    • 5a Vedejs E, Driver ST. J. Am. Chem. Soc. 1993; 115: 3358
    • 5b Anbu N, Nagarjun N, Jacob M, Kalaiarasi JM. V. K, Dhakshinamoorthy A. Chemistry 2019; 1: 69
    • 5c Mali SM, Bhaisare RD, Gopi HN. J. Org. Chem. 2013; 78: 5550
  • 6 Winkler JD, Rouse MB, Greaney MF, Harrison SJ, Jeon YT. J. Am. Chem. Soc. 2002; 124: 9726
  • 7 Corey EJ, Wu YJ. J. Am. Chem. Soc. 1993; 115: 8871
  • 8 Xu S, Held I, Kempf B, Mayr H, Steglich W, Zipse H. Chem. Eur. J. 2005; 11: 4751
  • 9 Fujihara R, Nakata K. ChemistrySelect 2019; 4: 75
    • 10a Chandra KL, Saravanan P, Singh RK, Singh VK. Tetrahedron 2002; 58: 1369
    • 10b Zareyee D, Alizadeh P, Ghandali MS, Khalilzadeh MA. Can. J. Chem. 2012; 90: 464
    • 10c Kalla RM. N, Reddy SS, Kim I. Catal. Lett. 2019; 149: 2696
    • 10d Chaubey SA, Mishra R. Chem. Pap. 2020; 74: 3259
    • 10e Khan AT, Choudhury LH, Ghosh S. Eur. J. Org. Chem. 2005; 2782
    • 10f Khana AT, Islam S, Majee A, Chattopadhyay T, Ghosh S. J. Mol. Catal. A: Chem. 2005; 239: 158
    • 10g Hajipour AR, Karimi H, Karimzadeh M. Monatsh. Chem. 2014; 145: 1461
    • 10h Chutia R, Chetia B. New. J. Chem. 2018; 42: 15200
    • 10i Khaligh NG, Mihankhah T, Johan MR, Juan JC. Phosphorus, Sulfur, Silicon Relat. Elem. 2019; 194: 866
    • 10j Khaligh NG. RSC Adv. 2013; 3: 99
    • 10k Rajabi F, Saidi MR. Synth. Commun. 2005; 35: 483
    • 10l Kadam ST, Kim SS. Synthesis 2008; 267
    • 10m Basumatary G, Bez G. Tetrahedron Lett. 2017; 58: 4312
  • 11 Chen JS, Sankar A, Lin YJ, Huang PH, Liao CH, Wu SS, Wu HR, Luo SY. RSC Adv. 2019; 9: 33853
  • 12 Bols M, Pedersen CM. Beilstein J. Org. Chem. 2017; 13: 93
    • 13a Corey EJ, Venkateswarlu A. J. Am. Chem. Soc. 1972; 94: 6190
    • 13b Corey EJ, Cho H, Rücker C, Hua DH. Tetrahedron Lett. 1981; 22: 3455
    • 13c Smrček J, Pohl R, Jahn U. Org. Biomol. Chem. 2017; 15: 9408
    • 13d Bartoszewicz A, Kalek M, Nilsson J, Hiresova R, Stawinski J. Synlett 2008; 37
    • 14a Bruynes CA, Jurriens TK. J. Org. Chem. 1982; 47: 3966
    • 14b Karimi B, Golshani B. J. Org. Chem. 2000; 65: 7228
    • 14c Shirini F, Zolfigol MA, Abedini M. Monatsh. Chem. 2009; 140: 61
    • 14d Joseph AA, Verma VP, Liu XY, Wu CH, Dhurandhare VM, Wang CC. Eur. J. Org. Chem. 2012; 744
    • 14e Wang C.-C, Lee J.-C, Luo S.-Y, Kulkarni SS, Huang Y.-W, Lee C.-C, Chang K.-L, Hung S.-C. Nature 2007; 446: 896
    • 14f Du W, Kulkarni SS, Gervay-Hague J. Chem. Commun. 2007; 2336
    • 14g Chen J.-S, Pantawane AR, Huang P.-H, Liu J.-W, Sankar A, Lin Y.-J, Liu YH, Wu H.-R, Luo S.-Y. Eur. J. Org. Chem. 2020; 5580
    • 15a Oskooie HA, Heravi MM, Tehrani MH, Behbahani FK, Heravi OM. Phosphorus, Sulfur, Silicon Relat. Elem. 2009; 184: 1729
    • 15b Kadam ST, Kim SS. Green Chem. 2010; 12: 94
    • 15c Firouzabadi H, Iranpoor N, Amani K, Nowrouzi F. J. Chem. Soc., Perkin Trans. 1 2002; 2601
    • 15d Amantini D, Fringuelli F, Pizzo F, Vaccaro L. J. Org. Chem. 2001; 66: 6734
    • 15e Rajagopal G, Lee HB, Kim SS. Tetrahedron 2009; 65: 4735
    • 15f Jereb M. Tetrahedron 2012; 68: 3861
    • 15g Sarpe VA, Kulkarni SS. Org. Lett. 2014; 16: 5732
    • 16a Nicolaou KC, Yang Z, Liu JJ, Ueno H, Nantermet PG, Guy RK, Claiborne CF, Renaud J, Couladouros EA, Paulvannan K, Sorensen EJ. Nature 1994; 367: 630
    • 16b Visser RG, Bos HJ. T, Brandsma L. Recl. Trav. Chim. Pays-Bas 1980; 99: 70
    • 16c Kurita K, Hirakawa M, Kikuchi S, Yamanaka H, Yang J. Carbohydr. Polym. 2004; 56: 333
  • 17 Chang KL, Zulueta MM. L, Lu XA, Zhong YQ, Hung SC. J. Org. Chem. 2010; 75: 7424
    • 18a Jereb M, Lakner J. Tetrahedron 2016; 72: 5713
    • 18b Akita M, Kakinuma N, Moro-oka Y. J. Organomet. Chem. 1988; 348: 91
    • 19a Shtelman AV, Becker JY. Tetrahedron 2011; 67: 1135
    • 19b Downey CW, Johnson MW, Lawrence DH, Fleisher AS, Tracy KJ. J. Org. Chem. 2010; 75: 5351
  • 20 Qin L, Hu B, Neumann KD, Linstad EJ, McCauley K, Veness J, Kempinger JJ, DiMagno SG. Eur. J. Org. Chem. 2015; 5919
  • 21 Sakurada I, Yamasaki S, Göttlich R, Iida T, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2000; 122: 1245
    • 22a Chen J.-S, Ke Y.-F, Lin H.-Y, Lin W, Yen W.-C, Wu H.-R, Luo S.-Y. Synthesis 2021; 53: 2000
    • 22b Pantawane AR, Thul M, Lin Y.-J, Lin M, Lin W, Julakanti SR, Wu H.-R, Luo S.-Y. Catalysts 2021; 11: 825