Abstract
A practical method has been developed for conversion of unprotected and unmodified aldoses to aldo-benzimidazoles and aldo-naphthimidazoles. Using iodine as an oxidant or promoter in acetic acid solution, a series of mono-, di-, and trialdoses, including those containing carboxyl and acetamido groups, undergo an oxidative condensation reaction with o-phenylenediamine or 2,3-naphthalenediamine at room temperature to give the aldo-benzimidazole and aldo-naphthimidazole products in high yields. No cleavage of the glycosidic bond occurs under such mild reaction conditions. The composition analysis of saccharides is realized by the HPLC analysis of the fluorescent naphthimidazole derivatives.
References
Jun 1, 1970·Chemical Reviews·L B Townsend, G R Revankar
Apr 25, 2000·Nucleosides, Nucleotides & Nucleic Acids·G A FreemanR J Harvey
Sep 10, 2002·Biomacromolecules·Rachel Auzély-VeltyMarguerite Rinaudo
Feb 1, 2003·The Journal of Organic Chemistry·Jiun-Jie Shie, Jim-Min Fang
Jun 21, 2003·Organic Letters·Lori A Maggio-HallTadhg P Begley
Oct 6, 2005·Carbohydrate Research·Byung Y Yang, Rex Montgomery
Nov 8, 2005·Analytical Biochemistry·Kalyan R Anumula
May 24, 2006·Carbohydrate Research·Kim LarsenKnud J Jensen
Mar 17, 2007·The Journal of Organic Chemistry·Jiun-Jie Shie, Jim-Min Fang
Citations
Jun 21, 2011·Journal of Natural Products·Tzong-Huei LeeYu-Min Ju
Aug 10, 2012·Organic Letters·Gary A Molander, Kehinde Ajayi
Feb 19, 2016·Journal of Biomedical Science·Ting-Lin YenJoen-Rong Sheu
Mar 12, 2011·Journal of Mass Spectrometry : JMS·Yu-Ling ChangYuan Chuan Lee
Sep 30, 2016·Molecular Diversity·Priyabrata RoyAnimesh Pramanik
Jan 5, 2017·Chemical & Pharmaceutical Bulletin·Eito YoshiokaHideto Miyabe
Jun 19, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chien-Yuan KuoWen-Bin Yang
May 2, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wei-Ting HungWen-Bin Yang
Mar 26, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chunchi LinWen-Bin Yang
Jan 19, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chunchi LinWen-Bin Yang
Dec 5, 2009·Rapid Communications in Mass Spectrometry : RCM·Chunchi LinWen-Bin Yang
Oct 16, 2014·Organic & Biomolecular Chemistry·Maryam NourisefatAli Khalafi-Nezhad
Jun 21, 2020·SLAS Technology·Wei-Ting HungWen-Bin Yang
Apr 11, 2012·Chemistry : a European Journal·Prakash T ParvatkarSantosh G Tilve
Sep 28, 2017·International Journal of Molecular Medicine·Yi ChangJiun-Yi Li
Dec 17, 2008·Organic & Biomolecular Chemistry·Pravin R LikharSukla Biswas
Oct 19, 2013·The Journal of Organic Chemistry·Suvendu SamantaPapu Biswas
Apr 3, 2014·The Journal of Organic Chemistry·Gunaganti NareshTadigoppula Narender
Aug 29, 2019·ACS Omega·Soheila Khajeh DangolaniAli Khalafi-Nezhad
Dec 13, 2019·Organic Letters·Jiao LiMaoluo Gan