Synthesis, Inhaltsverzeichnis Synthesis 2024; 56(07): 1175-1182DOI: 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 Padmashri Rabha , Rajib Panchadhayee∗ Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik 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 Key wordsacetone - carbohydrates - 2,2-dimethoxypropane - GR-SO3H - O-isopropylidene acetals - sustainability Volltext Referenzen 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 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 Zusatzmaterial Zusatzmaterial Supporting Information