TMDS as a Dual??Purpose Reductant in the Regioselective Ring Cleavage of Hexopyranosyl Acetals to Ethers
…, W Dayoub, GR Chen, M Lemaire
Index: Zhang, Yin-Jie; Dayoub, Wissam; Chen, Guo-Rong; Lemaire, Marc Green Chemistry, 2011 , vol. 13, # 10 p. 2737 - 2742
Full Text: HTML
Citation Number: 3
Abstract
Abstract 1, 1, 3, 3-Tetramethyldisiloxane (TMDS) has been developed as an excellent dual- purpose reductant for the highly regioselective ring cleavage of various hexopyranosyl 4, 6- O-acetals with Cu (OTf) 2 or AlCl 3 to afford the corresponding primary and secondary ethers. Its application to the concise synthesis of carbohydrate-based surfactants is highlighted.
Related Articles:
[Jones, Ray V.H.; Lindsell, W. Edward; Palmer, Daniel D.; Preston, Peter N.; Whitton, Alan J. Tetrahedron Letters, 2005 , vol. 46, # 50 p. 8695 - 8697]
New method for the synthesis of benzyl alkyl ethers mediated by FeSO4
[Joshi, Girdhar; Adimurthy, Subbarayappa Synthetic Communications, 2011 , vol. 41, # 5 p. 720 - 728]
[Boyer, Bernard; Keramane, El-Mehdi; Roque, Jean-Pierre; Pavia, Andre A. Tetrahedron Letters, 2000 , vol. 41, # 16 p. 2891 - 2894]
[Argouarch, Gilles; Grelaud, Guillaume; Roisnel, Thierry; Humphrey, Mark G.; Paul, Frederic Tetrahedron Letters, 2012 , vol. 53, # 37 p. 5015 - 5018]
Efficient method for the reductive cleavage of acetals and ketals with Zn (BH4) 2/Me3SiCl
[Kotsuki, Hiyoshizo; Ushio, Yasuyuki; Yoshimura, Naka; Ochi, Masamitsu Journal of Organic Chemistry, 1987 , vol. 52, # 12 p. 2594 - 2596]