RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2024; 56(07): 1175-1182
DOI: 10.1055/a-2218-7604
DOI: 10.1055/a-2218-7604
paper
Emerging Trends in Glycoscience
Efficient Preparation of O-Isopropylidene Derivatives of Carbohydrates Catalyzed by Sulfonated Graphene (GR-SO3H) as a Sustainable Acid Catalyst
Abstract
Sulfonated graphene (GR-SO3H) has emerged as a mild, efficient and sustainable catalyst for the preparation of O-isopropylidene derivatives of unprotected and anomeric-protected carbohydrates with acetone and 2,2-dimethoxypropane at room temperature. This methodology not only provides excellent yields but also reduces reaction times, and it demonstrates exceptional recyclability, allowing the catalyst to be reused multiple times.
Key words
acetone - carbohydrates - 2,2-dimethoxypropane - GR-SO3H - O-isopropylidene acetals - sustainabilitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2218-7604.
- Supporting Information
Publikationsverlauf
Eingereicht: 04. Oktober 2023
Angenommen nach Revision: 28. November 2023
Accepted Manuscript online:
28. November 2023
Artikel online veröffentlicht:
18. Dezember 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Guo J, Ye X.-S. Molecules 2010; 15: 7235
- 1b Protective Groups in Organic Synthesis, 4th Ed. Wuts PG, Greene TW. John Wiley & Sons Inc; Hoboken: 2007
- 2 Clode DM. Chem. Rev. 1979; 79: 491
- 3 Stick RV. Carbohydrates: The Sweet Molecules of Life . Academic Press; New York: 2001: 55
- 4 Yamanoi T, Oda Y, Matsuda S, Yamazaki I, Matsumura K, Katsuraya K, Watanabe M, Inazu T. Tetrahedron 2006; 62: 10383
- 5 Veeneman GH. In Carbohydrate Chemistry . Boons G.-J. Blackie Academic & Professional; London: 1998: 141-142
- 6a De Belder AN. Adv. Carbohydr. Chem. 1965; 20: 219
- 6b De Belder AN. Adv. Carbohydr. Chem. Biochem. 1977; 34: 179
- 7 Roslund MU, Klika KD, Lehtila RL, Taehtinen P, Sillanpaeae R, Leino R. J. Org. Chem. 2004; 69: 18
- 8a Alam MA, Vankar YD. Tetrahedron Lett. 2008; 49: 5534
- 8b Garegg PJ. In Prep. Carbohydr. Chem. . Hanessian S. Marcel Dekker; New York: 1997: 3
- 9 Goi A, Bruzzese T, Notarianni AF, Riva M, Ronchini A. Arzneim.-Forsch. 1979; 29: 986
- 10 Legler G, Pohl S. Carbohydr. Res. 1986; 155: 119
- 11a Yadav VK, Agrawal D. Chem. Commun. 2007; 48: 5232
- 11b Pattenden G, González MA, Little PB, Millan DS, Plowright AT, Tornos JA, Ye T. Org. Biomol. Chem. 2003; 1: 4173
- 12 Fischer E. Ber. Dtsch. Chem. Ges. 1895; 28: 1145
- 13 Schmidt OT. Methods Carbohydr. Chem. 1963; 2: 318
- 14 Kitamura M, Isobe M, Ichikawa Y, Goto T. J. Am. Chem. Soc. 1984; 106: 3252
- 15 Rauter AP, Ramôa-Ribeiro F, Fernandes AC, Figueiredo JA. Tetrahedron 1995; 51: 6529
- 16 Asakura J.-I, Matsubara Y, Yoshihara M. J. Carbohydr. Chem. 1996; 15: 231
- 17 Kartha KP. R. Tetrahedron Lett. 1986; 27: 3415
- 18 Nair PR. M, Shah PM, Sreenivasan B. Starch/Staerke 1981; 33: 384
- 19a Pfaff PK, Paust J, Hartmann H. BASF A.-G. Ger. Offen. DE 3,505,150
- 19b (cl. C07H9/04), 21 August 1986, Appl. 15 February 1985 (CA 106:18984r)
- 20 Singh PP, Gharia MM, Dasgupta F, Srivastava HC. Tetrahedron Lett. 1977; 439
- 21 Hering KW, Karaveg K, Moremen KW, Pearson WH. J. Org. Chem. 2005; 70: 9892
- 22 Lal B, Gidwani RM, Rupp RH. Synthesis 1989; 711
- 23 Manzo E, Barone G, Parrilli M. Synlett 2000; 887
- 24 Schmid CR, Bryant JD, Dowlatzedah M, Phillips JL, Prather DE, Schautz RD, Sear NL, Vianco CS. J. Org. Chem. 1991; 56: 4056
- 25 Rajput VK, Mukhopadhyay B. Tetrahedron Lett. 2006; 47: 5939
- 26 Pedatella S, Guaragna A, D’Alonzo D, DeNisco M, Palumbo G. Synthesis 2006; 305
- 27 Lin C.-C, Jan M.-D, Weng S.-S, Lin C.-C, Chen C.-T. Carbohydr. Res. 2006; 341: 1948
- 28 Khan AT, Khan MM, Adhikary A. Carbohydr. Res. 2011; 346: 673
- 29 Khan AT, Khan MM. Carbohydr. Res. 2010; 345: 154
- 30 Mandal S, Verma PR, Mukhopadhyay B, Gupta P. Carbohydr. Res. 2011; 346: 2007
- 31 Khiangte V, Ghanashyam B. Tetrahedron Lett. 2011; 52: 3759
- 32 Oger N, Lin YF, Le Grognec E, Rataboul F, Felpin FX. Green Chem. 2016; 18: 1531
- 33 Thombal RS, Jadhav VH. J. Carbohydr. Chem. 2016; 35: 57
- 34 Vessally E, Hassanpour A, Hosseinzadeh-Khanmiri R, Babazadeh M, Abolhasani J. Monatsh. Chem. 2017; 148: 321
- 35 Brahmayya M, Dai SA, Suen S.-Y. Sci. Rep. 2017; 7: 4675
- 36 Hosseini MS, Masteri-Farahani M. Tetrahedron 2021; 86: 132083
- 37 Rabha P, Sharma A, Panchadhayee R. Synlett 2023; in press DOI: 10.1055/a-2166-0400.
- 38 Islam DA, Barman K, Jasimuddin S, Acharya H. ChemElectroChem 2017; 4: 3110
- 39 Rong YW, Zhang QH, Wang W, Li BL. Bull. Korean Chem. Soc. 2014; 35: 2165
- 40 Gelas J. Carbohydr. Res. 1978; 67: 371
- 41 Haines AH. Carbohydr. Res. 1965; 1: 214
- 42 Michaud T, Ray JC, Chou S, Gelas J. Carbohydr. Res. 1997; 299: 253