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DOI: 10.1055/s-0042-1751501
Application of N-Bromosuccinimide in Carbohydrate Chemistry
Abstract
This article describes the use of N-bromosuccinimide in different organic group transformations in carbohydrate chemistry. A comprehensive discussion on the synthesis of deoxysugars through selective O-benzylidene fragmentation, photobromination, halogenation, oxidation, and polymerisation of different carbohydrate moieties with the aid of N-bromosuccinimide (NBS) is presented. The use of NBS in the most significant glycosylation methods and in oligosaccharide synthesis is also discussed.
Publication History
Received: 20 July 2023
Accepted after revision: 31 August 2023
Article published online:
19 October 2023
© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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References
- 1 Amat M, Hadida S, Sathyanarayana S, Bosc J. Org. Synth., Coll. Vol. IX 1998; 417
- 2 Gilow HW, Burton DE. J. Org. Chem. 1981; 46: 2221
- 3 Brown WD, Gouliaev AH. Org. Synth. 2005; 81: 98
- 4 Mitchell RH, Lai YH, Williams RV. J. Org. Chem. 1979; 44: 4733
- 5 Corey EJ, Ishiguro M. Tetrahedron Lett. 1979; 2745
- 6 Keillor JW, Huang X. Org. Synth., Coll. Vol. X 2004; 549
- 7 Ramachandran MS, Easwaramoorthy D, Rajasingh V, Vivekanandam TS. Bull. Chem. Soc. Jpn. 1990; 63: 2397
- 8 Song X, Ju H, Zhao C, Lasanajak Y. Bioconjugate Chem. 2014; 25: 1881
- 9 Harpp DN, Bao LQ, Coyle C, Gleason JG, Horovitch S. Org. Synth., Coll. Vol. VI 1988; 190
- 10a Wohl A. Ber. Dtsch. Chem. Ges. 1919; 52: 51
- 10b Ziegler K, Schenck G, Krockow EW, Siebert A, Wenz A, Weber H. Justus Liebigs Ann. Chem. 1942; 551: 1
- 10c Djerassi C. Chem. Rev. 1948; 43: 271
- 11 Haufe G, Alvernhe G, Laurent A, Ernet T, Goj O, Kröger S, Sattler A. Org. Synth., Coll. Vol. X 2004; 128
- 12 Goswami S, Dey S, Jana S, Adak AK. Chem. Lett. 2004; 33: 916
- 13 Rajagopal R, Jarikote DV, Lathoti RJ, Daniel T, Srinivasan KV. Tetrahedron Lett. 2003; 44: 1815
- 14 Crawforth CM, Burling S, Fairlamb IJ. S, Taylor RJ. K, Whitwood AC. Chem. Commun. 2003; 2194
- 15 Reddy S, Narender M, Nageswar YV. D, Rao R. Synthesis 2005; 714
- 16 Narender M, Reddy MS, Rao KR. Synthesis 2004; 1741
- 17a Zhou H, Jiang J, Zhang K. Journal of Polymer Science: Part A: Polymer Chemistry 2005; 43: 2567
- 17b Zhang W, Zhu X, Zhu J. e-Polymers 2004; 4: 020
- 18 Prasad PK, Reddi RN, Sudalai A. Org. Lett. 2016; 18 (3): 500
- 19 Khazaei A, Rostami A, Raiatzadeh A. J. Chin. Chem. Soc. 2007; 54: 1029
- 20 Filler R. Chem. Rev. 1963; 63: 21
- 21a Gupta S, Bera S, Mondal D. J. Org. Chem. 2020; 85: 2635
- 21b Limbani B, Mondal D, Bera S. Sonochemical protocol for protection and deprotection of functional groups in organic synthesis. In Green Sustainable Process for Chemical and Environmental Engineering and Science: Sonochemical Organic Synthesis. Inamuddin, Elsevier; Amsterdam: 2019
- 21c Bera S, Mondal D, Martin JT, Singh M. Carbohydr. Res. 2015; 410: 599
- 22 Motawia MS, Marcussen J, Moller BL. J. Carbohydr. Chem. 1995; 14: 1279
- 23 Donohoe TJ, Flores A, Bataille CJ. R, Churruca F. Angew. Chem. Int. Ed. 2009; 48: 6507
- 24 Panchadhayee R, Misra AK. J. Carbohydr. Chem. 2010; 29: 76
- 25 Sharma GV. M, Reddy VG, Krishna PR, Sanker AR, Kunwar AC. Tetrahedron 2002; 58: 3801
- 26 Silva S, Fernández EM. S, Mellet CO, Tatibouët A, Rauter AP, Rollin P. Eur. J. Org. Chem. 2013; 7941
- 27 Sun XF, Sun RC, Zhao L, Sun JX. J. Appl. Polym. Sci. 2004; 92: 53
- 28 Singh M. Int. J. Carbohydr. Chem. 2014; 783521
- 29 Ichiyanagi T, Sakamoto N, Ochi K, Yamasaki R. J. Carbohydr. Chem. 2009; 28: 53
- 30a Rodriguez MA, Boutureira O, Arnes X, Matheu MI, Diaz Y, Castillon S. J. Org. Chem. 2005; 70: 10297
- 30b Boutureira O, Matheu MI, Diaz Y, Castillon S. RSC Adv. 2014; 4: 19794
- 31 Liu CF, Xiong DC, Ye XS. J. Org. Chem. 2014; 79: 4676
- 32 Blattner R, Ferrier RJ. J. Chem. Soc., Perkin Trans. 1 1980; 1523
- 33 Nicolaou KC, Delle RE, Papahatjis DP, Randall JL. J. Am. Chem. Soc. 1984; 106: 4189
- 34 Tseng H, Furuhata K, Sakamoto M. Carbohydr. Res. 1995; 270: 149
- 35 Yousuf SK, Hussain A, Sharma DK, Wani AH, Singh B, Mukherjee D, Taneja SC. J. Carbohydr. Chem. 2011; 30: 61
- 36 Lah HU, Mir SA, Hussain G, Wani RA, Yousuf SK. J. Chem. Sci. 2022; 134: 18
- 37 Hanessian S. Carbohydr. Res. 1966; 2: 86
- 38a Hanessian S, Plessas NR. J. Org. Chem. 1969; 34: 1035
- 38b Hanessian S, Plessas NR. J. Org. Chem. 1969; 34: 1045
- 38c Hanessian S, Plessas NR. J. Org. Chem. 1969; 34: 1053
- 39a Hanessian S. Org. Synth. 1987; 65: 243
- 39b Hanessian S. Some Approaches to the Synthesis of Halodeoxy Sugars . In Deoxy Sugars . Hanessian S. Advances in Chemistry Series 74; American Chemical Society; Washington: 1968: 159-201
- 40 Failla DL, Hullar TL, Siskin SB. Chem. Commun. 1966; 716
- 41 Hullar TL, Siskin SB. J. Org. Chem. 1970; 35: 225
- 42 Binkley RW, Goewey GS, Johnston J. J. Org. Chem. 1984; 49: 992
- 43 Gelas J. Adv. Carbohydr. Chem. Biochem. 1981; 39: 71
- 44 Jeppesen LM, Lundt I, Pedersen C. Acta Chem. Scand. 1973; 27: 3579
- 45a Dang HS, Roberts BP, Sekhon J, Smits TM. Org. Biomol. Chem. 2003; 1: 1330
- 45b Cai Y, Dang HS, Roberts BP. J. Chem. Soc., Perkin Trans. 1 2002; 2449
- 45c Roberts BP, Smits TM. Tetrahedron Lett. 2001; 42: 3663
- 45d Fielding AJ, Franchi P, Roberts BP, Smits TM. J. Chem. Soc., Perkin Trans. 2 2002; 155
- 46 McNulty J, Wilson J, Rochon AC. J. Org. Chem. 2004; 69: 563
- 47a Yadav RN, Hossain MdF, Das A, Srivastava AK, Banik BKr. Catal. Rev. 2022; 18: 1 , DOI:10.1080/01614940.2022.2041303
- 47b Nicolaou KC, Seitz SP, Papahatjis DP. J. Am. Chem. Soc. 1983; 105: 2430
- 48 Sasaki M, Tachibana K. Tetrahedron Lett. 1991; 32: 6873
- 49 Roush WR, Lin X, Straub JA. J. Org. Chem. 1991; 56: 1649
- 50 Toshima K, Nozaki Y, Tatsuta K. Tetrahedron Lett. 1991; 32: 6887
- 51 Pawar NJ, Wang L, Higo T, Bhattacharya C, Kancharla PK, Zhang F, Baryal K, Huo C.-X, Liu J, Linhardt RJ, Huang X, Hsieh-Wilson LC. Angew. Chem. Int. Ed. 2019; 58: 18577
- 52 Yu HN, Furukawa J.-I, Ikeda T, Wong C.-H. Org. Lett. 2004; 6: 723
- 53a Qin Z.-H, Li H, Cai M.-S, Li Z.-J. Carbohydr. Res. 2002; 337: 31
- 53b Kadokawa JI, Yamamoto M, Tagaya H, Chiba K. Carbohydr. Lett. 2001; 4: 97
- 54a Emmadi M, Kulkarni SS. Org. Biomol. Chem. 2013; 11: 3098
- 54b Emmadi M, Kulkarni SS. Nat. Protoc. 2013; 8: 1870
- 55 Patil PS, Cheng T.-JR, Zulueta MM. L, Yang S.-T, Lico LS, Hung S.-C. Nat. Commun. 2015; 6: 7239
- 56 Qin C, Schumann B, Zou X, Pereira CL, Tian G, Hu J, Seeberger PH, Yin J. J. Am. Chem. Soc. 2018; 140: 3120
- 57 Meguro Y, Noguchi M, Li G, Shoda S.-i. Org. Lett. 2018; 20: 76
- 58 Li H, Mao H, Chen C, Xu Y, Meng S, Sun T, Zong C. Front. Chem. 2022; 1039731