A Practical Silicon-Free Strategy for Differentiation of Hydroxy Groups in Arabinofuranose Derivatives

Dedicated to the memory of the late Professor Leon V. Backinowsky

Abstract

Effective differentiation of 3,5-diol system and 2-hydroxy group in arabinofuranose derivatives, which is required for the preparation of building blocks useful for the synthesis of nucleoside analogues and oligosaccharide fragments of mycobacterial arabinogalactan and lipoarabinomannan, was achieved by using 3,5-di-O-benzoyl-1,2-O-benzylidene-β-d-arabinofuranose or 3-O-(chloroacetyl)-β-d-arabinofuranose 1,2,5-orthobenzoate, both readily accessible from inexpensive methyl α-d-arabinofuranoside via the corresponding glycosyl bromides. The use of expensive organosilicon protecting groups is completely avoided in this novel strategy, a feature that makes it amenable to scale-up.

Key words

carbohydrates - protecting groups - acetals - oligosaccharides - nucleosides

• References

• 1a Joe M, Bai Y, Nacario RC, Lowary TL. J. Am. Chem. Soc. 2007; 129: 9885
• 1b Zhu X, Kawatkar S, Rao Y, Boons G.-J. J. Am. Chem. Soc. 2006; 128: 11948
• 1c Ishiwata A, Akao H, Ito Y. Org. Lett. 2006; 8: 5525
• 1d Lee YJ, Lee K, Jung EH, Jeon HB, Kim KS. Org. Lett. 2005; 7: 3263
• 1e Crich D, Pedersen CM, Bowers AA, Wink DJ. J. Org. Chem. 2007; 72: 1553
• 1f Fraser-Reid B, Lu J, Jayaprakash KN, López JC. Tetrahedron: Asymmetry 2006; 17: 2449
• 1g Liang X.-Y, Deng L.-M, Liu X, Yang J.-S. Tetrahedron 2010; 66: 6687
• 1h Marotte K, Sanchez S, Bamhaoud T, Prandi J. Eur. J. Org. Chem. 2003; 3587
• 1i Yin H, D’Souza FW, Lowary TL. J. Org. Chem. 2002; 67: 892
• 1j Gadikota RR, Callam CS, Appelmelk BJ, Lowary TL. J. Carbohydr. Chem. 2003; 22: 459
• 1k Mereyala HB, Hotha S, Gurjar MK. Chem. Commun. (Cambridge) 1998; 685
• 1l Tam P.-H, Lowary TL. Carbohydr. Chem. 2010; 36: 38 ; and references cited therein
• 2 Health Topics: Tuberculosis . World Health Organization; Geneva: 2012. http://www.who.int/topics/tuberculosis/en (accessed March 15, 2012)
• 3 Pathak AK, Pathak V, Bansal N, Maddry JA, Reynolds RC. Tetrahedron Lett. 2001; 42: 979
• 4 Mei X, Ning J. Synlett 2005; 2267
• 5 Podvalnyy NM, Sedinkin SL, Abronina PI, Zinin AI, Fedina KG, Torgov VI, Kononov LO. Carbohydr. Res. 2011; 346: 7
• 6 Ishiwata A, Ito Y. J. Am. Chem. Soc. 2011; 133: 2275
• 7 Dahlman O, Garegg PJ, Mayer H, Schramek S. Acta Chem. Scand., Ser. B 1986; 40: 15
• 8 Kochetkov NK, Byramova NÉ, Tsvetkov YE, Backinowsky LV. Tetrahedron 1985; 41: 3363
• 9 Jung ME, Xu Y. Org. Lett. 1999; 1: 1517
• 10a Ness RK, Fletcher HG. J. Am. Chem. Soc. 1958; 80: 2007
• 10b Callam CS, Lowary TL. J. Chem. Educ. 2001; 78: 73
• 11 Byramova NÉ , Ovchinnikov MV, Backinowsky LV, Kochetkov NK. Carbohydr. Res. 1983; 124: C8
• 12 Abronina PI, Podvalnyy NM, Melnikova TM, Zinin AI, Fedina KG, Kachala VI, Torgov VI, Kononov LO, Panferzev EA, Baranova EV, Mochalov VV, Dyatlova VI, Biketov SF. Russ. Chem. Bull. 2010; 59: 2333
• 13a Pathak T. Chem. Rev. 2002; 102: 1623
• 13b Zatsepin TS, Romanova EA, Oretskaya TS. Russ. Chem. Rev. 2004; 73: 701
• 14a Antiviral Nucleosides: Chiral Synthesis and Chemotherapy. Chu CK. Elsevier; Amsterdam: 2003
• 14b De Clercq E. Antiviral Res. 2005; 67: 56
• 14c Mathéa C, Gosselin G. Antiviral Res. 2006; 71: 276
• 15a Wuts PG. M, Greene TW. Greene’s Protective Groups in Organic Synthesis . 4th ed. Wiley-Interscience; Hoboken: 2007: 239
• 15b Wuts PG. M, Greene TW. Greene’s Protective Groups in Organic Synthesis . 4th ed. Wiley-Interscience; Hoboken: 2007: 353
• 15c Kocieński PJ. Protecting Groups . 3rd ed. Thieme; Stuttgart: 2005: 171