Selective Hydrolysis of Aryl Esters under Acidic and Neutral Conditions by a Synthetic Aspartic Protease Mimic

ACS Catalysis ◽  
2021 ◽  
pp. 3938-3942
Author(s):  
Ishani Bose ◽  
Yan Zhao
Author(s):  
G. G. Sivets ◽  
A. V. Sivets

The method for synthesis of N-pentofuranosyl oxazolines was developed from the protected 1,2-O-acetonides of D-xylofuranose, -ribofuranose, and -arabinofuranose using boron trifluoride diethyl etherate, acetonitrile, and potassium hydrogen difluoride. A possible mechanism of the catalyzed reaction of acylated acetonides with acetonitrile in the presence of Lewis acid was considered in terms of the activation and cleavage of the 1,3-dioxalane part of the xylose derivative fol- lowed by the conversions of intermediates to α-isooxazoline. The hydrolysis reactions of N-α-glycosyl oxazolines were stud- ied in the acidic and neutral conditions. N-α-xylofuranosyl acetamide derivatives were prepared in high yields as a result of selective hydrolysis of protected α-xylofuranosyl isooxazolines in the neutral conditions.


2014 ◽  
Vol 11 (6) ◽  
pp. 684-689 ◽  
Author(s):  
Jing-Yuan LIU ◽  
He-Shui YU ◽  
Bing FENG ◽  
Li-Ping KANG ◽  
Xu PANG ◽  
...  

1975 ◽  
Vol 53 (6) ◽  
pp. 869-877 ◽  
Author(s):  
B. Rossall ◽  
R. E. Robertson

The temperature dependence of the rate of hydrolysis of benzoic, phthalic, and succinic anhydrides have been determined in H2O and D2O under "neutral" conditions. Corresponding data have been obtained for methyl trifluoroacetate. While both series supposedly react by the same BAc2 mechanism, remarkable differences are made obvious by this investigation. Possible sources of such differences are proposed.


1997 ◽  
Vol 38 (17) ◽  
pp. 2981-2984 ◽  
Author(s):  
Véronique Le Boisselier ◽  
Michèle Postel ◽  
Elisabet Duñach

1983 ◽  
Vol 23 (5) ◽  
pp. 471 ◽  
Author(s):  
A. Haas ◽  
W. Wanzke ◽  
N. Welcman

ChemInform ◽  
2010 ◽  
Vol 42 (2) ◽  
pp. no-no
Author(s):  
Purba Mukerjee ◽  
Mohammed Abid ◽  
Frank C. Schroeder

2003 ◽  
Vol 42 (26) ◽  
pp. 8618-8620 ◽  
Author(s):  
Felix H. Zelder ◽  
Andriy A. Mokhir ◽  
Roland Krämer

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