Stereoselective Hydrolysis of p-Nitrophenyl Glycoside by Boronic Acid

1998 ◽  
Vol 27 (11) ◽  
pp. 1077-1078 ◽  
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Yohji Nakatsuji ◽  
Isao Ikeda
ChemInform ◽  
2010 ◽  
Vol 30 (13) ◽  
pp. no-no
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Takeru Ohe ◽  
Toshiyuki Kida ◽  
Wanbin Zhang ◽  
Yohji Nakatsuji ◽  
Isao Ikeda

2021 ◽  
pp. 112408
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Susana Chávez ◽  
Pedro Mederos ◽  
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Antonio Monroy-Noyola

1991 ◽  
Vol 55 (11) ◽  
pp. 2865-2870
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Ryohei Komaki ◽  
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Shigeyasu Nabeshima

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Tetrahedron ◽  
1981 ◽  
Vol 37 (1) ◽  
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2011 ◽  
Vol 64 (11) ◽  
pp. 1425 ◽  
Author(s):  
Donald S. Matteson

Hydrolysis of diisopropyl (bromomethyl)boronate followed by reaction with pinanediol provides an efficient route to pinanediol (hydroxymethyl)boronate (12), a useful intermediate for asymmetric synthesis. The stability of (hydroxymethyl)boronic acid (10) and its ester 12 have been examined by NMR spectroscopy. Heating for 1 h in acidic D2O does not degrade 10 and only affects the pinanediol moiety of 12. Base does not degrade 10 or 12 in several days at 20–25°C, but converts either to DCH2OD and CH3OD in a few h at 90–98°C, with a large H/D isotope effect. Pinanediol (bromomethyl)boronate with sodium hydroxide in D2O yields a gross mixture of products.


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