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Synthesis 2013; 45(4): 471-478
DOI: 10.1055/s-0032-1318106
DOI: 10.1055/s-0032-1318106
paper
Water-Dependent Reduction of Carbohydrate Azides by Dithiothreitol
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Publication History
Received: 01 November 2012
Accepted after revision: 21 December 2012
Publication Date:
18 January 2013 (online)
Dedicated to Professor Genrikh A. Tolstikov on the occasion of his 80th birthday
Abstract
Dithiothreitol efficiently reduces carbohydrate azides in aqueous acetonitrile to give good-to-excellent yields of the corresponding amines or, after N-acetylation, acetamides. This reduction can proceed in either the presence or the absence of a base.
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References
- 1a Paulsen H, Schleyer A, Mathieux N, Meldal M, Bock K. J. Chem. Soc., Perkin Trans. 1997; 281
- 1b Vohra Y, Buskas T, Boons G.-J. J. Org. Chem. 2009; 74: 6064
- 2a Hasegawa A, Nagahama T, Kiso M. Carbohydr. Res. 1992; 235: C13
- 2b Ogawa S, Ito H, Ogawa T, Iwasaki S, Suami T. Bull. Chem. Soc. Jpn. 1983; 56: 2319
- 2c Ishida HK, Ishida H, Hasegawa A. Carbohydr. Res. 1994; 260: C1
- 2d Westerduin P, van Boom JH, van Boeckel CA. A, Beetz T. Carbohydr. Res. 1985; 137: C4
- 2e Paulsen H, Tietz H. Angew. Chem. 1982; 94: 934
- 2f Popsavin M, Torović L, Svirčev M, Kojić V, Bogdanović G, Popsavin V. Bioorg. Med. Chem. Lett. 2006; 16: 2773
- 2g Du W, Gervay-Hague J. Org. Lett. 2005; 7: 2063
- 2h Schombs M, Park FE, Du W, Kulkarni SS, Gervay-Hague J. J. Org. Chem. 2010; 75: 4891
- 3a Peterson MA, Nilsson BL, Sarker S, Doboszewski B, Zhang W, Robins MJ. J. Org. Chem. 1999; 64: 8183
- 3b Dullenkopf W, Ritter G, Fortunato SR, Old LJ, Schmidt RR. Chem. Eur. J. 1999; 5: 2432
- 3c Afonsoa CA. M, Barrosa MT, Maycock CD. Tetrahedron 1999; 55: 801
- 3d Seiferta J, Ogawa T, Ito Y. Tetrahedron Lett. 1999; 40: 6803
- 3e Harwig CW, Hoffman TZ, Wentworth AD, Janda KD. Bioorg. Med. Chem. Lett. 2000; 10: 915
- 3f Robins MJ, Doboszewski B, Nillson BL, Peterson MA. Nucleosides Nucleotides 2000; 19: 69
- 4 Jaquinet J.-C. Carbohydr. Res. 1990; 199: 153
- 5a Zhou X.-T, Forestier C, Goff RD, Li C, Teyton L, Bendelac A, Savage PB. Org. Lett. 2002; 4: 1267
- 5b Tang W, Muderawan IW, Ong T.-T, Ng S.-C. Tetrahedron: Asymmetry 2007; 18: 1548
- 5c Friedrich-Bochnitschek S, Waldmann H, Kunz H. J. Org. Chem. 1989; 54: 751
- 6a Mullen LB, Sutherland JD. Angew. Chem. Int. Ed. 2007; 46: 4166
- 6b Wojczewski C, Schwarzer K, Engels JW. Helv. Chim. Acta 2000; 83: 1268
- 6c Kuo G.-H, Prouty C, Murray WV, Pulito V, Jolliffe L, Cheung P, Varga S, Evangelisto M, Wang J. J. Med. Chem. 2000; 43: 2183
- 6d Figueroa-Pérez S, Schmidt RR. Carbohydr. Res. 2000; 328: 95
- 6e Knapp S, Zhao D. Org. Lett. 2000; 2: 4037
- 7 Rösch M, Herzner H, Dippold W, Wild M, Vestweber D, Kunz H. Angew. Chem. Int. Ed. 2001; 40: 3836
- 8a Yan L, Kahne D. J. Am. Chem. Soc. 1996; 118: 9239
- 8b Litjens RE. J. N, den Heeten R, Timmer MS. M, Overkleeft HS, van der Marel GA. Chem. Eur. J. 2005; 11: 1010
- 8c van Boeckel CA. A In Modern Synthetic Methods, Scheffold R. Vol. 6. Verlag Helvetica Chimica Acta; Basel: 1992: 439
- 9a Boer J, Blount KF, Luedtke NW, Elson-Schwab L, Tor Y. Angew. Chem. Int. Ed. 2005; 44: 927
- 9b Kleinert M, Röckendorf N, Lindhorst TK. Eur. J. Org. Chem. 2004; 3931
- 9c Lindhorst TK, Bruegge K, Fuchs A, Sperling O. Beilstein J. Org. Chem. 2010; 6: 801
- 9d Lindhorst TK, Kötter S, Krallmann-Wenzel U, Ehlers S. J. Chem. Soc., Perkin Trans. 2001; 823
- 10 Rao Y, Venot A, Swayze EE, Griffey RH, Boons G.-J. Org. Biomol. Chem. 2006; 4: 1328
- 11a Ke W, Whitfield DM, Brisson J.-R, Enright G, Jarrel HC, Wu W.-g. Carbohydr. Res. 2005; 340: 355
- 11b Lee J.-C, Lu X.-A, Kulkarni SS, Wen Y.-S, Hung S.-C. J. Am. Chem. Soc. 2004; 126: 476
- 12 Cheng H, Cao X, Xian M, Fang L, Cai TB, Ji JJ, Tunac JB, Sun D, Wang PG. J. Med. Chem. 2005; 48: 645 ; yields of the Pd-catalyzed hydrogenation were not reported in this publication
- 13 Meinjohanns E, Meldal M, Jensen T, Werdelin O, Galli-Stampino L, Mouritsen S, Bock K. J. Chem. Soc., Perkin Trans. 1997; 871
- 14 Greilich U, Brescello R, Jung K.-H, Schmidt RR. Liebigs Ann. 1996; 663
- 15 Komarova BS, Tsvetkov YE, Pier GB, Nifantiev NE. J. Org. Chem. 2008; 73: 8411
- 16a Reardon JE, Crouch RC, St John-Williams L. J. Biol. Chem. 1994; 269: 15999
- 16b Handlon AL, Oppenheimer NJ. Pharm. Res. 1988; 5: 297
- 17 Mironov YV, Sherman AA, Nifantiev NE. Mendeleev Commun. 2008; 1: 241
- 18 Alberta R, Daxa K, Pleschko R, Stütz AE. Carbohydr. Res. 1985; 13: 282
- 19 Klemer A, Wilbers H. Liebigs Ann. Chem. 1985; 2328
- 20 Smelt KH, Harrison AJ, Biggadike K, Müller M, Prout K, Watkin DJ, Fleet GW. J. Tetrahedron Lett. 1999; 40: 3259
- 21 Yuan H, Fairchild CR, Liang X, Kingston DG. I. Tetrahedron 2000; 56: 6407
- 22 Patroni JJ, Stick RV. Aust. J. Chem. 1985; 38: 947
- 23a Zhou Y, Lin F, Chen J, Yu B. Carbohydr. Res. 2006; 341: 1619
- 23b Guthrie RD, Murphy D. J. Chem. Soc. 1963; 5288
- 24 Bartra M, Urpí F, Vilarrasa J. Tetrahedron Lett. 1987; 28: 5941
- 25 Sharma M, Bernackia RJ, Hillmana MJ, Korytnyk W. Carbohydr. Res. 1993; 240: 85
- 26 Sukhova EV, Dubrovskii AV, Tsvetkov YE, Nifantiev NE. Russ. Chem. Bull. 2007; 56: 1655
- 27 Tsvetkov YE, Shashkov AS, Knirel YA, Zäringer U. Carbohydr. Res. 2001; 335: 221
- 28 Tsvetkov YE, Backinowsky LV, Kochetkov NK. Bioorg. Khim. 1991; 17: 1534