Determination of the absolute configuration of monosaccharides by 1H NMR spectroscopy of their per-O-(S)-2-methylbutyrate derivatives

1997 ◽  
Vol 300 (3) ◽  
pp. 199-206 ◽  
Author(s):  
William S. York ◽  
Stephen Hantus ◽  
Peter Albersheim ◽  
Alan G. Darvill
1977 ◽  
Vol 32 (5) ◽  
pp. 589-593 ◽  
Author(s):  
Reiner Luckenbach ◽  
Hans-H. Bechtolsheimer

The preparation and separation into diastereomers of tbutyl-phenyl-phosphinic acid (—)-menthyl ester (1a) is reported. The diastereomeric purity as well as the absolute configuration at phosphorus of 1 a can be deduced from the detailed analysis of the 1H NMR spectra of samples of 1a differing in their diastereomer ratios.


2011 ◽  
Vol 6 (5) ◽  
pp. 1934578X1100600 ◽  
Author(s):  
Tatyana N. Makarieva ◽  
Larisa K. Shubina ◽  
Alla G. Guzii ◽  
Natalya V. Ivanchina ◽  
Vladimir A. Denisenko ◽  
...  

A study has been made of the 1H NMR spectra of peracetylated β-glucopyranosides and α-arabinopyranosides obtained by reaction of D- and L-glucoses, and L- and D-arabinoses with either ( R)- or ( S)-2-octanols. The obtained and literature data show that 1H NMR spectra may be used to determine the absolute configuration of the aglycone moieties of some alicyclic glycosides without the need to synthesize derivatives with chiral reagents, as long as the absolute configuration of their monosaccharide moiety is known or vice versa. Spectra of marine steroid glycosides and their acetates containing glycosylated side chains as alicyclic fragments were also examined. It was shown that analysis of 1H NMR spectra for the determination of the absolute configuration is more applicable in the cases when glycosides have the same substitution in the D-ring of the aglycone moiety.


2016 ◽  
Vol 18 (16) ◽  
pp. 4084-4087 ◽  
Author(s):  
Si-Yuan Shao ◽  
Fan Zhang ◽  
Ya-Nan Yang ◽  
Zi-Ming Feng ◽  
Jian-Shuang Jiang ◽  
...  

2008 ◽  
Vol 19 (8) ◽  
pp. 989-997 ◽  
Author(s):  
Alessandra Ammazzalorso ◽  
Giancarlo Bettoni ◽  
Barbara De Filippis ◽  
Marialuigia Fantacuzzi ◽  
Letizia Giampietro ◽  
...  

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