Detail of "53167-11-6"

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Carbon-13-carbon-13 spin coupling constants in aldoses enriched with 13C at the terminal hydroxymethyl carbon: effect of coupling pathway structure of JCC in carbohydrates

Carbon-13-carbon-13 spin coupling constants in aldoses enriched with 13C at the terminal hydroxymethyl carbon: effect of coupling pathway structure of JCC in carbohydrates.. Wu, Jian; Bondo, Paul B.; Vuorinen, Tapani; Serianni, Anthony S. (Dep. Chem. Biochem., Univ. Notre Dame, Notre Dame, IN 46556, USA). J. Am. Chem. Soc., 114(9), 3499-505 (English) 1992. CODEN: JACSAT. ISSN: 0002-7863. DOCUMENT TYPE: Journal CA Section: 33 (Carbohydrates) Section cross-reference(s): 22 Eight aldohexoses (allo, altro, galacto, gluco, gulo, ido, manno, talo), four aldopentoses (arabino, lyxo, ribo, xylo), and two aldotetroses (eryhtro, threo) were prepd. with 13C-enrichment (99 atom-% 13C) at the terminal hydroxymethyl (CH2OH) carbon. High-resoln. 53167-11-6 and 14762-74-4 are cas registry numbers of chemicals which are used as reagents here. 1H-decoupled 13C-NMR spectra were obtained at 75 and 125 MHz in order to obtain one-bond (1JCC) and longer range (2JCC, 3JCC) 13C-13C spin coupling consts. involving the terminal carbons of the more abundant furanose and pyranose forms of these monosaccharides in 2H2O. In some cases spectral interpretation was assisted by the use of one-dimensional INADEQ2aTE 13C spectra. The effect of aldopyranose and aldofuranose ring structure and conformation on the magnitudes of these couplings, esp. 2JCCC and 3JCCCC, was probed. Results show that 2JCCC is highly affected by the orientation of terminal hydroxyl substituents along the C-C-C coupling pathway and that 3JCCCC is not only affected by mol. dihedral angle (i.e., Karplus relationship) but also by substituent geometry along the C-C-C-C coupling pathway. .