Stereo- and Site-Selective Acylation in Carbohydrate Synthesis

Stephanie A. Blaszczyk; Xiaolei Li; Peng Wen; Weiping Tang

doi:10.1055/a-2214-7557

Synlett, Table of Contents

Synlett 2024; 35(15): 1745-1762
DOI: 10.1055/a-2214-7557

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Stereo- and Site-Selective Acylation in Carbohydrate Synthesis

Stephanie A. Blaszczyk

^aSchool of Pharmacy, University of Wisconsin-Madison, 777 Highland Ave, Madison, WI 53705, USA

^bDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, WI 53706, USA

,

Xiaolei Li

^aSchool of Pharmacy, University of Wisconsin-Madison, 777 Highland Ave, Madison, WI 53705, USA

,

Peng Wen

^aSchool of Pharmacy, University of Wisconsin-Madison, 777 Highland Ave, Madison, WI 53705, USA

,

Weiping Tang∗

^aSchool of Pharmacy, University of Wisconsin-Madison, 777 Highland Ave, Madison, WI 53705, USA

^bDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, WI 53706, USA

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Abstract

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Abstract

Carbohydrates are synthetically challenging molecules with vital biological roles in all living systems. To better understand the biological functions of this fundamentally important class of molecules, novel methodologies are needed, including site-selective functionalization and glycosylation reactions. This account describes our efforts toward the development of novel methodologies for site-selective functionalization of carbohydrates and stereoselective glycosylation through various acylation reactions.

Keywords

carbohydrate - esterification - catalysis - site-selective functionalization - stereoselective

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References

References

1a Bertozzi CR, Kiessling LL. Science 2001; 291: 2537
1b Stallforth P, Lepenies B, Adibekian A, Seeberger PH. J. Med. Chem. 2009; 52: 5561
1c Ernst B, Magnani JL. Nat. Rev. Drug Discovery 2009; 8: 661
1d Dwek RA. Chem. Rev. 1996; 96: 683

2a Hartwig JF. Acc. Chem. Res. 2017; 50: 549
2b Toste FD, Sigman MS, Miller SJ. Acc. Chem. Res. 2017; 50: 609
2c Blaszczyk SA, Tang W. Chem 2017; 3: 722
2d Dimakos V, Taylor MS. Chem. Rev. 2018; 118: 11457
2e Blaszczyk SA, Homan TC, Tang W. Carbohydr. Res. 2019; 471: 64
2f Yamatsugu K, Kanai M. Chem. Rev. 2023; 123: 6793

3 Achmatowicz O, Bukowski P, Szechner B, Zwierzchowska Z, Zamojski A. Tetrahedron 1971; 27: 1973
4 Wang HY, Yang K, Bennett SR, Guo SR, Tang W. Angew. Chem. Int. Ed. 2015; 54: 8756
5 Schmidt B, Hauke S. Eur. J. Org. Chem. 2014; 1951
6 Matsushima Y, Kino J. Eur. J. Org. Chem. 2010; 2206
7 Thomson MI, Nichol GS, Lawrence AL. Org. Lett. 2017; 19: 2199
8 Blume F, Liu Y.-C, Thiel D, Deska J. J. Mol. Catal. B: Enzym. 2016; 134: 280
9 Della-Felice F, Sarotti AM, Krische MJ, Pilli RA. J. Am. Chem. Soc. 2019; 141: 13778
10 Zhu Z, Wang H.-Y, Simmons C, Tseng P.-S, Qiu X, Zhang Y, Duan X, Yang J.-K, Tang W. Adv. Synth. Catal. 2018; 360: 595

11a Babu RS, O’Doherty GA. J. Am. Chem. Soc. 2003; 125: 12406
11b Zheng J, O’Doherty GA. 2.14 - De Novo Synthesis of Oligosaccharides Via Metal Catalysis . In Comprehensive Glycoscience, 2nd ed. Barchi JJ. Jr. Elsevier; Oxford: 2021: 435-463

12 Wang HY, Yang K, Yin D, Liu C, Glazier DA, Tang W. Org. Lett. 2015; 17: 5272
13 Taylor JE, Bull SD, Williams JM. J. Chem. Soc. Rev. 2012; 41: 2109

14a Birman VB, Li X. Org. Lett. 2006; 8: 1351
14b Li X, Jiang H, Uffman EW, Guo L, Zhang Y, Yang X, Birman VB. J. Org. Chem. 2012; 77: 1722

15a Nakata K, Gotoh K, Ono K, Futami K, Shiina I. Org. Lett. 2013; 15: 1170
15b Shiina I, Nakata K, Ono K, Onda Y, Itagaki M. J. Am. Chem. Soc. 2010; 132: 11629
15c Shiina I, Nakata N. Tetrahedron Lett. 2007; 48: 8314

16 Babu RS, Qian C, Kang S.-W, Zhou M, O’Doherty GA. J Am. Chem. Soc. 2012; 134: 11952
17 Ortiz A, Benkovics T, Beutner GL, Shi Z, Bultman M, Nye J, Sfouggatakis C, Kronenthal DR. Angew. Chem. Int. Ed. 2015; 54: 7185
18 Song W, Zhao Y, Lynch JC, Kim H, Tang W. Chem. Commun. 2015; 51: 17475
19 Zhu Z, Glazier DA, Yang D, Tang W. Adv. Synth. Catal. 2018; 360: 2211

20a Elshahawi SI, Shaaban KA, Kharel MK, Thorson JS. A. Chem. Soc. Rev. 2015; 44: 7591
20b Hulst MB, Grocholski T, Neefjes JJ. C, van Wezel GP, Metsä-Ketelä M. Nat. Prod. Rep. 2022; 39: 814
20c Deane C. Nat. Chem. Biol. 2016; 12: 467
20d Bellucci MC, Volonterio A. Antibiotics 2020; 9: 504

21 Li X, Liu P, Houk KN, Birman VB. J. Am. Chem. Soc. 2008; 130: 13836
22 Wang HY, Simmons CJ, Zhang Y, Smits AM, Balzer PG, Wang S, Tang W. Org. Lett. 2017; 19: 508
23 Glazier DA, Schroeder JM, Liu J, Tang W. Adv. Synth. Catal. 2018; 360: 464

24a Wang HY, Blaszczyk SA, Xiao G, Tang W. Chem. Soc. Rev. 2018; 47: 681
24b Lawandi J, Rocheleau S, Moitessier N. Tetrahedron 2016; 72: 6283

25a David S, Hanessian S. Tetrahedron 1985; 41: 643
25b Oshima K, Kitazono E, Aoyama Y. Tetrahedron Lett. 1997; 38: 5001
25c Lee D, Taylor MS. J. Am. Chem. Soc. 2011; 133: 3724
25d Gouliaras C, Lee D, Chan L, Taylor MS. J. Am. Chem. Soc. 2011; 133: 13926
25e Ren B, Ramström O, Zhang Q, Ge J, Dong H. Chem. Eur. J. 2016; 22: 2481
25f Ren B, Lv J, Zhang Y, Tian J, Dong H. ChemCatChem 2017; 9: 950
25g Li R, Tang H, Wan L, Zhang X, Fu Z, Liu J, Yang S, Jia D, Niu D. Chem 2017; 3: 834
25h Shang W, Mou Z, Tang H, Zhang X, Fu Z, Niu D. Angew. Chem. Int. Ed. 2018; 57: 314
25i Rao VU. B, Wang C, Demarque DP, Grassin C, Otte F, Merten C, Strohmann C, Loh CC. J. Nat. Chem. 2023; 15: 424

26 Xiao G, Cintron-Rosado GA, Glazier DA, Xi BM, Liu C, Liu P, Tang W. J. Am. Chem. Soc. 2017; 139: 4346

27a Robinson ER. T, Fallan C, Simal C, Slawina AM. Z, Smith AD. Chem. Sci. 2013; 4: 2193
27b Yan W, Zheng M, Xu C, Chen F. Green Synth. Catal. 2021; 2: 329

28 Hao H, Qi X, Tang W, Liu P. Org. Lett. 2021; 23: 4411
29 Xiao X, Zeng J, Fang J, Sun J, Li T, Song Z, Cai L, Wan Q. J. Am. Chem. Soc. 2020; 142: 5498

30a Lian G, Zhang X, Biao Y. Carbohydr. Res. 2015; 403: 13
30b Stick RV, Williams SJ. Carbohydrates: The Essential Molecules of Life 2009
30c Escopy S, Demchenko AV. Chem. Eur. J. 2022; 28: e202103747

31 Blaszczyk SA, Xiao G, Wen P, Hao H, Wu J, Wang B, Carattino F, Li Z, Glazier DA, McCarty BJ, Liu P, Tang W. Angew. Chem. Int. Ed. 2019; 58: 9542
32 Dohi H, Nishida Y. Trends in Glycoscience and Glycotechnology 2014; 26: 119
33 Li ZT, Gildersleeve JC. J. Am. Chem. Soc. 2006; 128: 11612

34a Lahmann M, Oscarson S. Can. J. Chem. 2002; 80: 889
34b Crich D, Li W. Org. Lett. 2007; 72: 7794

35 Moya-Lopez JF, Elhalem E, Recio R, Alvarez E, Fernandez I, Khiar N. Org. Biomol. Chem. 2015; 13: 1904
36 Zhou D, Mattner J, Cantu VIII, Schrantz N, Yin N, Gao Y, Sagiv Y, Hudspeth K, Wu Y.-P, Yamashita T, Teneberg S, Wang D, Proia RL, Levery SB, Savage PB, Teyton L, Bendelac A. Science 2004; 306: 1786
37 Alanazi AS, James E, Mehellou Y. ACS Med. Chem. Lett. 2019; 10: 2
38 Dai Q, Chen R. Heteroat. Chem. 1997; 8: 279

39a Liu S, Zhang Z, Xie F, Butt NA, Sun L, Zhang W. Tetrahedron: Asymmetry 2012; 23: 329
39b Wang L, Du Z, Wu Q, Jin R, Bian Z, Kang C, Guo H, Ma X, Gao L. Eur. J. Org. Chem. 2016; 11: 2024
39c Ye X, Peng L, Bao X, Tan C, Wang H. Green Synth. Catal. 2021; 2: 6

40 DiRocco DA, Ji Y, Sherer EC, Klapars A, Reibarkh M, Dropinski J, Mathew R, Maligres P, Hyde AM, Limanto J, Brunskill A, Ruck RT, Campeau L.-C, Davies IW. Science 2017; 356: 426
41 Glazier DA, Schroeder JM, Blaszczyk SA, Tang W. Adv. Synth. Catal. 2019; 361: 3729

42a Peng P, Schmidt RR. Acc. Chem. Res. 2017; 50: 1171
42b Leng W, Yao H, He J, Liu X. Acc. Chem. Res. 2018; 51: 628
42c Yang Y, Zhang X, Yu B. Nat. Prod. Rep. 2015; 32: 1331

43 Wang H.-Y, Simmons CJ, Blaszczyk SA, Balzer PG, Luo R, Duan X, Tang W. Angew. Chem. Int. Ed. 2017; 56: 15698

44a Imagawa H, Kinoshita A, Fukuyama T, Yamamoto H, Nishizawa M. Tetrahedron Lett. 2006; 47: 4729
44b Zhang Y, Wang P, Song N, Li M. Carbohydr. Res. 2013; 381: 101
44c Li Y, Yang Y, Yu B. Tetrahedron Lett. 2008; 49: 3604
44d Koppolu SR, Niddana R, Balamurugan R. Org. Biomol. Chem. 2015; 13: 5094
44e Mishra B, Neralkar M, Hotha S. Angew. Chem. Int. Ed. 2016; 55: 7786

45a Mensah EA, Nguyen HM. J. Am. Chem. Soc. 2009; 131: 8778
45b Mensah EA, Yu F, Nguyen HM. J. Am. Chem. Soc. 2010; 132: 14288

46a Zhu Y, Yu B. Angew. Chem. Int. Ed. 2011; 50: 8329
46b Tang Y, Li J, Zhu Y, Li Y, Yu B. J. Am. Chem. Soc. 2013; 135: 18396
46c Yu B. Acc. Chem. Res. 2018; 51: 507

47 Wen P, Simmons CJ, Ma ZX, Blaszczyk SA, Balzer PG, Ye W, Duan X, Wang HY, Yin D, Stevens CM, Tang W. Org. Lett. 2020; 22: 1495

48a Koide K, Ohno M, Kobayashi S. Tetrahedron Lett. 1991; 32: 7065
48b Furukawa H, Koide K, Takao K.-i, Kobayashi S. Chem. Pharm. Bull. 1998; 46: 1244

49 Ye W, Stevens CM, Wen P, Simmons CJ, Tang W. J. Org. Chem. 2020; 85: 16218

50a Wu J, Li X, Qi X, Duan X, Cracraft WL, Guizei IA, Liu P, Tang W. J. Am. Chem. Soc. 2019; 141: 19902
50b Wu J, Jia P, Kuniyil R, Liu P, Tang W. Angew. Chem. Int. Ed. 2023; 62: e202307144

51 Li X, Wu J, Tang W. J. Am. Chem. Soc. 2022; 144: 3727