Glycosylation of α-amino acids by sugar acetate donors with InBr 3. Minimally competent Lewis acids
…, B Anglin, M Ferracane, J Hogan, L Cooney, R Polt
Index: Lefever, Mark R.; Szab, Lajos Z.; Anglin, Bobbi; Ferracane, Michael; Hogan, Joanna; Cooney, Lauren; Polt, Robin Carbohydrate Research, 2012 , vol. 351, p. 121 - 125
Full Text: HTML
Citation Number: 12
Abstract
A simplified method for the preparation of Fmoc-serine and Fmoc-threonine glycosides for use in O-linked glycopeptide synthesis is described. Lewis acids promote glycoside formation, but also promote undesired reactions of the glycoside products. Use of 'minimally competent'Lewis acids such as InBr3 promotes the desired activation catalytically, and with greatly reduced side products from sugar peracetates.
Related Articles:
Indium (III) Triflate: A Highly Efficient Catalyst for Reactions of Sugars [1]
[Giri, Santosh Kumar; Verma, Monika; Kartha, K. P. Ravindranathan Journal of Carbohydrate Chemistry, 2008 , vol. 27, # 8-9 p. 464 - 478]
[Malik, Satish; Shah, Krupesh J.; Ravindranathan Kartha Carbohydrate Research, 2010 , vol. 345, # 7 p. 867 - 871]
[Korth, Hans-Gert; Sustmann, Reiner; Groeninger, Kay Stefan; Leisung, Michael; Giese, Bernd Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4364 - 4369]
[Ghosh, Rina; Maiti, Swarupananda; Chakraborty, Arijit Tetrahedron Letters, 2004 , vol. 45, # 36 p. 6775 - 6778]
[Mukherjee, Debaraj; Shah, Bhahwal Ali; Gupta, Pankaj; Taneja, Subhash Chandra Journal of Organic Chemistry, 2007 , vol. 72, # 23 p. 8965 - 8968]