Synthesis, Inhaltsverzeichnis Synthesis 2013; 45(14): 1946-1949DOI: 10.1055/s-0033-1339174 practical synthetic procedures © Georg Thieme Verlag Stuttgart · New York 4′,6′-O-Benzylidene- and 4′,6′-O-p-Methoxybenzylidene-α,β-cellobiose and Their Hexa-O-β-benzoyl Derivatives Xiaowei Lu NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA Fax: +1(301)4805703 eMail: kpn@helix.nih.gov , Deepak Sail NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA Fax: +1(301)4805703 eMail: kpn@helix.nih.gov , Pavol Kováč* NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA Fax: +1(301)4805703 eMail: kpn@helix.nih.gov › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract The preparation of 4′,6′-O-benzylidenecellobiose has been improved and its p-methoxybenzylidene counterpart was prepared in a similar way. As with other alkylidene derivatives of sugars, the corresponding per-O-benzoates are versatile intermediates in carbohydrate synthesis, allowing, after hydrolytic cleavage or opening of the phenylidene ring, regioselective manipulation of hydroxyl groups in cellobiose, or access to various derivatives of lactose. Key words Key wordssynthetic methods - carbohydrate chemistry - protecting groups - regioselectivity Volltext Referenzen References 1 Fügedi P, Lipták A, Nanási P, Szejtli J. Carbohydr. Res. 1982; 104: 55 2 Garegg PJ, Hultberg H, Wallin S. Carbohydr. Res. 1982; 108: 97 3 Johansson R, Samuelsson B. J. Chem. Soc., Perkin Trans. 1 1984; 2371 4 Panchadhayee R, Misra AK. Synlett 2010; 1193 5 Sakagami M, Hamana H. Tetrahedron Lett. 2000; 41: 5547 6 Tanaka K, Fukase K. Synlett 2007; 164 7 Mani NS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1989; 28: 602 8 Kantlehner W, Gutbrod HD. Liebigs Ann. Chem. 1979; 1362 9 Kantlehner W, Gutbrod HD, Gross P. Liebigs Ann. Chem. 1979; 522 10 Evans ME. Carbohydr. Res. 1972; 21: 473 11 Murguía C, Vaillard SE, Ricardo JG. Synthesis 2001; 1093 12 Luo S.-Y, Kulkarni SS, Chou C.-H, Liao W.-M, Hung S.-C. J. Org. Chem. 2006; 71: 1226 13 Sail D, Kováč P. Carbohydr. Res. 2012; 357: 47 14 Chretien Synth. Commun. 1990; 20: 1589 15 Debenham SD, Toone EJ. Tetrahedron: Asymmetry 2000; 11: 385 16 Crich D, Yao Q, Bowers AA. Carbohydr. Res. 2006; 341: 1748 17 Zhang Y.-J, Dayoub W, Chen G.-R, Lemaire M. Eur. J. Org. Chem. 2012; 1960 18 Lipták A, Czegényi I, Harangi J, Nanási P. Carbohydr. Res. 1979; 73: 327 19 Hanessian S, Plessas NR. J. Org. Chem. 1969; 34: 1045 20 Hanessian S, Plessas NR. J. Org. Chem. 1969; 34: 1053 21 Casu B, Reggiani M, Gallo GG, Vigevani A. Tetrahedron Lett. 1964; 2839 Zusatzmaterial Zusatzmaterial Supporting Information
